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<h1><a href="https://archiveofourown.org/works/24796813">New Gurl In Town</a> by <a class='authorlink' href='https://archiveofourown.org/users/GavinIsaNuisance/pseuds/GavinIsaNuisance'>GavinIsaNuisance</a></h1>

<table class="full">

<tr><td><b>Series:</b></td><td>Shemales Topping Sissies [2]</td></tr>

<tr><td><b>Category:</b></td><td>Original Work</td></tr>

<tr><td><b>Genre:</b></td><td>Anal, Anal Fingering, Anal Sex, Anal Virgin, Ass Play, Ass to Mouth, Butt Plugs, F/F, F/M, Face-Fucking, Face-Sitting, Female on Male, Feminization, Forced Feminization, Futanari, Futanari on Male, Gen, Pegging, Public Humiliation, Semi-Public Sex, Shemale, Shemale on Male, Spanking, Strap-Ons, blowjob, cum on face, dildo, dominant female, male sub, panty boy, rimjob, sissification, sissy boy</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>In-Progress</td></tr>

<tr><td><b>Published:</b></td><td>2020-06-19</td></tr>

<tr><td><b>Updated:</b></td><td>2020-09-27</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-04 11:07:27</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>3</td></tr>

<tr><td><b>Words:</b></td><td>24,413</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/24796813</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/GavinIsaNuisance/pseuds/GavinIsaNuisance</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Andy has a deep desire to be turned into a sissy, his request and his burdening roommate situation are both answered by Carol, a feisty smoking hot shamble who helps train Andy and make him into a perfect sissy slut, but Andy's heart belongs to another, his dominatrix neighbor Riley. Armed with a new sub persona: Bianca, he finds some confidence to start a secret relationship with the girl of his dreams while Carol isn't the wiser.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Andy/Riley, Carol (Shemale)/Andy</td></tr>

<tr><td><b>Series:</b></td><td>Shemales Topping Sissies [2]</td></tr>

<tr><td><b>Series URL:</b></td><td>https://archiveofourown.org/series/1793206</td></tr>

<tr><td><b>Comments:</b></td><td>1</td></tr>

<tr><td><b>Kudos:</b></td><td>29</td></tr>

</table>

<a name="section0001"><h2>1. Roommates, am I right?</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>This work is entirely fictitious. Any similarities to actual persons living or dead is purely coincidental and entirely unintentional. All persons depicted in a naked/and or sexual nature are 18 and up.</p>
    </blockquote></div><div class="userstuff module">
    
    <p>The city of Los Angeles, California. A place once regarded as the focal point for entertainment and movie stardom now reduced to an over-taxed, grimy, drug-infested mess of its once prominent self. While not the birthplace of the California Dream it was certainly what made it famous and eventually infamous. Now the California dream has moved to Austin, Atlanta, Portland, Denver, and in the case of Bryan Cranston: Albuquerque.</p><p>The average Angeleno most likely has them self a main job and a side-hustle. Often times that side-hustle is multiple side-hustles. The average Angeleno will never be able to afford a house, let alone an apartment and therefore finding roommates even if you've barely or even never met them before is becoming quite commonplace. Roommates are your best friend and worst enemy all at the same time. They assist in the paying of rent, but play loud music and hog all the hot water. Actually, the only real pro on this potentially long list of cons is they assist in the rent burden.</p><p>Far too often, Angeleno's get desperate for money and might take a chance on a new roommate or job they will definitely hate. For one Angeleno, this would distort his love life and change him forever. Which brings us away from the poetic exposition and into the crux of our story. Our cautiously witting protagonist is lifelong Los Angeles resident: Andrew Bairn, who often went by his formulaic childhood nickname: Andy. He was a shy boy, spindly and lanky, with a shy face. He had short dirty blonde hair, nary a freckle or wrinkle to be had. He possessed a very skinny frame, average to slightly below average penis size but where he shined, was his posterior as Andy had a bubbly man butt which he was obviously more impressed by than his dick.</p><p>Andy was born and raised in the San Fernando Valley; an earthquake prone, hot, mostly suburban part of Los Angeles just north of the Santa Monica Mountains and Hollywood Hills and thus away from most of the city's main hustle and bustle. He was raised in the Studio City neighborhood, nicknamed "Hebrew Heights", given its long stereotypical history as a haven for entertainment workers who more often than not: were Jewish. His parents were well-to-do yet Andy lived the life of a slacker, just getting by at North Hollywood high school. He managed to somehow get in the nearby California State University Northridge where at the age of nineteen, sick of his parents badgering him to get a job, he moved out and to the North Hills neighborhood not far from campus.</p><p>Andy quickly found that one needs money to do things and he lacked in many skills, but was able to secure a living doing various gig-economy based jobs while attending school. He briefly had a roommate, a longtime friend whose name is not important but who quickly moved out and into his new girlfriend's apartment. Which Segway's nicely into Andy's love life, or lack thereof. Andy was now twenty and still a virgin, largely due to his awkward appearance and spindly bod. But what was largely impacting Andy's lack of sex and reinforcing his virginity was his odd fetish which he kept secret. Andy was secretly into being dominated and humiliated by women.</p><p>He wasn't sure how he found himself in the thralls of being a bitch but he knew he enjoyed the fuck out of it. He always figured he had an ass for fucking and a dick for jerking off. If one were to peruse Andy's porn search history one would find many videos of usually men being dominated by a woman, usually in latex, dawning strap-ons and the like. He would watch them tie men up, step on their balls with high heels, pouring candle wax on their chests, fucking their asses with dildos and generally humiliating them. He was especially into men being feminized to look like a woman and then fucked with a strap-on.</p><p>Up until this point in his life however, Andy didn't actually get to enjoy his own fetish, besides jerking off to pornographies depicting it. He would peruse message boards for Doms and Subs and would usually depict him jerking off or spreading his ass cheeks on his bed and usually he would get responses from female Doms that wanted to fuck him or gay male tops who wanted the same. Andy did have one way to get close to achieving his fetish goals.</p><p>He had a neighbor.</p><p>Her name was Riley Consuelos. Her first name was actually Raimunda, but she went by Riley because people could spell and pronounce it easier and she didn't have time for name bullshit. She was a few years older than Andy, maybe two or three tops. She attended his high school rival Grant high, but they never really interacted. Riley was a Hispanic woman, slender and tall, with c-cup breasts, long dark hair usually with red highlights to piss off her traditionalist parents, mocha skin, smooth legs, and a tight booty, usually seen wearing some sort of metal band t-shirt and yoga pants. Riley too had a fetish which would fit in perfectly with Andy's, she was a Dom. Andy only knew this as their apartments were nearby, the walls were paper thin, and Riley along with her various sexual conquests were not exactly quiet. Riley also suffered through being unproductive and directionless in her life, but grew up without Andy's privilege. She worked as a waitress at a Buffalo Wild Wings in Sherman Oaks, a job which she so despised but was too lazy to quit and find anything better.</p><p>Riley was so lazy she rarely-if ever locked her front door, a thing nobody in LA ever does particularly when you live in such a questionable neighborhood. Andy was always curious as to what a Dom like Riley would have in her apartment and often found himself sneaking in just to take a peek. Her apartment was always a mess. Through Andy's violating investigations he came up with multiple jackpots; namely a few pairs of lacey panties and mesh stockings. He and Riley had a similar build so most of her undergarments closely fit Andy. Andy also would curiously come across Riley's various dildos, butt plugs, strap-on harnesses and vibrators but he never mustered up the gumption to ram any of the various phallic devices up his ass. He would merely take the panties and run.</p><p>Typically he would pilfer them from Riley's mess of a room where he would dress in the garb and take pics of himself to post them on the various forums he frequented. He would caption how he was a 'naughty girl who needed a spanking' and other such fetishistic catchphrases. He would take many lewd photos of himself in provocative positions. Typically when finished, he would return Riley's underwear and hosiery to its rightful messy place where Riley was ultimately too oblivious by the mess to notice them missing. A few thongs, a sexy garter belt, and a particular pair of fishnet stockings he kept but again, Riley never even noticed, or even cared to notice they had been taken, and would merely chalk it up to the mess as to them being missing.</p><p>Andy had kept these articles as he wanted to gain the necessary courage to "return" them to Riley with him wearing them so Riley would ultimately punish him for doing so, his life's very sad dream. Though he never went through with it as he was afraid Riley would instead call the police.</p><p>Indeed, Andy continued to live out his sure-to-be sad twenties still a virgin, with little direction in his life coupled with categorical loneliness. Made more difficult by the fact the only activity that truly gave him joy was committing petty larceny in order to satisfy the sexual urges he was too scared to act on. This of course changed.</p><p>As previously mentioned before transitioning into the sad state of affairs that was Andy's life, the spindly armed twenty year old needed a new roommate lest he not be able to afford his astronomically priced rent and forcing him to move back in with his parents, which at his age isn't entirely uncommon. After not being able to convince any friends to move in, whether they already had solid living arrangements or couldn't afford half the rent on their own; Andy then made the critical error of consulting the Internet to find a stranger to live with him. No place was better suited at finding such strangers than: Craigslist.</p><p>Andy soon had a bevy of applicants; a regular rogue's gallery of rejected Breaking Bad extras. He struck out with every male applicant he could find. Typically they didn't have a secure job, which Andy also did not possess but what he did possess was the will to work whereas many were beyond unemployable. Others either had a drug problem, were working on their current drug problem, or were just plain crazy. The last applicant he had was someone named Carol Larzaretta, which Andy found strange considering he was certain he put that he was preferably looking for a male roommate. He then found his interest piqued because she probably saw "preferably" and assumed he might think she would desperately apply in hopes of getting picked. Andy figured he wouldn't mind having a female roommate though it would be awkward as while he had two bedrooms there was only one bathroom.</p><p>Andy had another miserable day of roommate interviews but he had heard nothing from the so-called Carol, now assuming it was nearly a prank application. Late that evening there would be a knock at his door which will finally end the one-thousand six hundred words of exposition needed to get us here. Andy opened his front door.</p><p>"Yes, can I help…you?"</p><p>Andy stood there wide-eyed and in shock with his mouth slack-jawed almost in cartoonish fashion. There standing in the dimly lit hallway outside his apartment stood a woman with various pieces of matching luggage behind her.</p><p>"Hi. I'm Carol" she said, extending her hand.</p><p>Andy had to mentally slap himself. It was a woman! A real life woman! And not just any woman, this woman was hot! Carol stood an inch or two taller than Andy and was in her late twenties. She had long platinum blonde hair with dark roots, and a cute but very neutral face. Carol had massive DD cup breasts with a tight stomach, thick hips with a massive tushy. She wore a t-shirt with a pair of cherries on the front with very tight fitting jeans.</p><p>"Uh" Andy stammered.</p><p>"You are Andrew Bai—rn, right? Is that how you say it?"</p><p>"Uh-yeah, close enough. You're Carol Larzar—"</p><p>"Larzaretta. See, you tried to get me back" she joked. Andy nervously laughed as he had a rising boner he was trying to conceal. "Anyway, can you help me with my things?"</p><p>"Oh um, well, you need to—"</p><p>"Great, thanks."</p><p>Carol grabbed two suitcases and forced her way past Andy, leaving the spindly armed young man very confused. But, he was a little bitch after all and at the very least wanted to help. If anything, he could learn why Carol applied to his add in the first place. Andy grabbed a bag and took it inside.</p><p>"Yeah, so, I-I think you're confused. This is an application process. I'm interviewing potential roommates and—"</p><p>"Oh, did you fill the vacancy? I'm so sorry" Carol interjected.</p><p>"No-no, not yet. I-I-I'm still in the interviewing po—"</p><p>"Do you take cash? I read the rent is $1067 a month, right?"</p><p>Before Andy could stammer trying to look to find the application which he wrote, Carol grabbed a wad of rolled up bills from under her bra and shoved them into Andy's hand. He gulped like the sixteen year old pervert he truly was at heart, despite being twenty and having seen boobs before.</p><p>"Um, y-y-yeah."</p><p>"Go ahead, count it. It's all there" Carol assured him.</p><p>"Uh…" Andy trailed. It was mostly in twenties and tens but it seemed to be enough. "Y-yeah, usually I ask for a W-2, and like, take this to my landlord and then she gets back to me and if that's all good then—"</p><p>"So, my room's over here, right?" Carol asked, ignoring Andy. "I'm guessing it's the one with no bed, right? I'm kidding. I got one getting delivered tomorrow along with my dresser and shit. Don't worry I'll make sure they won't scuff anything up."</p><p>Andy walked down the hallway to what would be Carol's room where she was already starting to unpack. He took a moment to count the money, it was 1067 to the dollar. Sensing the rent would be due in a few days and him not having time to wait and see with the landlord, and coupling with Carol's obvious "not-taking-no-for-an-answer" mentality, Andy shrugged, and dug out a spare key from his pocket. "There's a $500 security deposit, too."</p><p>"Right-right. Sorry" Carol said, standing up. She dug into her pants pocket this time and pulled out five hundreds. Andy shrugged again, handing Carol the house key.</p><p>"So for next month, rent's due on the first, you can get it to me or the landlady, she's in apartment thirty-four."</p><p>"Yay! Oh thank you so much!" She gave Andy a deep hug, shoving the boy's head into her bosom. "You have no idea, I was like, literally about to be homeless."</p><p>"Well um, now you're not" Andy shrugged, getting another boob filled hug from his new sexy roommate.</p><p>"Again, I can't thank you enough, Andrew."</p><p>"Oh, thanks, but uh, call me Andy."</p><p>The next few weeks weren't so bad. Andy spent most of his day working his various gig-jobs and Carol was rarely-if ever home during the day too and was never home on the weekends. Both were also usually quiet. So far the arrangement was going great. One day, Andy came home to discover Carol cooking, which he found odd considering he never saw her cook or had any food in the kitchen. There was also a bottle of tequila sitting on the breakfast nook.</p><p>"Hey" Andy said.</p><p>"Hey yourself."</p><p>"What's all this?"</p><p>"Well, you've been so nice in just letting me stay instead of-you know, going through the whole pain-in-the-ass process that I wanted to do something nice. So, I'm making pasta with mussels in a tomato sauce."</p><p>"Wow, uh, thanks Carol."</p><p>"And it just wouldn't be a complete meal without something to take the edge off" she said, pouring Andy a shot of tequila.</p><p>"But, I'm not twenty-one, not for seven months."</p><p>"I won't tell if you won't" Carol winked.</p><p>Andy gulped, not wanting to be a wienie. He took the shot glass and did his best to knock it back, wincing as that cheap tequila taste coated his esophagus. Carol promptly poured him another shot. Andy took ginger sips from this one lest he vomit all over the place and definitely look like a wuss in front of his hot roommate.</p><p>The two ate and finished Carol's tequila, both very drunk from doing so. Andy more drunk than Carol. They found themselves on the couch, watching some phoned-in reality show on Netflix, but were really getting to know one another.</p><p>"So, you're Italian?" Andy asked Carol.</p><p>"My father. I am also German and Brazilian. I get my tits and ass from my Brazilian side" she slurred with a wink.</p><p>"Well I'm glad you noticed. I sure have" Andy added, taking another sip of liquid courage.</p><p>"So, what about you, Andy?"</p><p>"Me?"</p><p>"Yeah, you're young and shit. Got a girlfriend?"</p><p>"No" he groused.</p><p>"Boyfriend?"</p><p>Nope. I'm just a twenty year old virgin. There. I said it!" he took the last sip from the bottle.</p><p>"Don't get discouraged dude. You'll meet someone. Look, fucking all the time isn't what it's cracked up to be. Trust me" Carol explained.</p><p>"I-I'm trying to meet the right woman. I'm sorta into weird shit" he explained.</p><p>"Me too. But what are you into? And the laws of drinking say now you have to tell me" Carol explained, tricking the drunk boy.</p><p>"You won't tell nobody?" Andy asked.</p><p>"Swear."</p><p>"Okay" Andy tried to take another sip from the bottle, but there were none left. "I want a chick to fuck me with a strap-on. I'm inna that BDS-whatever shit."</p><p>Carol sat up on the couch more, piquing her interest. "Like, you want to be a sissy?"</p><p>"Yeah, that."</p><p>"Have you ever been feminized before? You know, dressed like a woman, then fucked?"</p><p>"Nope. Never done anything" Andy said conveniently leaving out stealing Riley's panties and stockings from her apartment. "Now you probably think I'm weird as shit, huh?"</p><p>"No. Not at all. It's okay to have those urges. It's kind of hot" she muttered the last part. "I'm sure you can find a girl in LA who's into that."</p><p>"I think I did. Our neighbor. She's super-hot. Like a bombshell. Her name's Riley" he slurred.</p><p>Before Carol could ask any follow-up questions, Andy had fallen fast asleep from all the alcohol swimming around in his bloodstream and liver. Carol looked over and saw Andy laying on his stomach, his ass was lifted up from his crotch resting on a couch pillow. She was curious, and thought a poor virgin like Andy deserved something, he was pretty hospitable after all. Carol slowly slid down his shorts and compression shorts underneath and got a good view of Andy's shaved nude rear.</p><p>She squeezed his cheeks and then spread them apart, revealing a shaved and puckered hole. Carol licked her lips. "Hey, Andy? Can I play with your ass?"</p><p>"Uh, yeah sssss" Danny trailed, barely audible.</p><p>Carol took that as a yes and then went to her room, and into her dresser, taking out a pink vibrator with cheetah spots adorned on it. She went over to Andy and opened his cheeks up. She got a second thought and put the vibrator aside, mesmerized by Andy's butt cheeks.</p><p>"Hmm, what an ass" Carol mused. "I can't possibly waste this tushy on a vibrator."</p><p>Carol smirked and lowered her pants and panties, and a nearly erect dick flopped free. Yup, Carol was a tranny. She didn't feel the need to reveal this fact to Andy because mostly it was a sore subject with her former roommates and figured it wouldn't come to moments like this, where she had someone who was into kinky fucking.</p><p>She also figured as Andy was into being sissified and fucked with dildos that her having a real cock probably wasn't exactly a huge turnoff, and she was too horny to really process her reasoning for keeping quiet about it. She put her dick between Andy's cheeks and started to run it along his crack, hot-dogging his cheeks. This motion made her really hard very fast yet the sleeping Andy didn't notice.</p><p>But before Carol could dip her head in to lube up his hole she had second thoughts. True, Andy had said yes but it was a very drunken passed out yes, definitely not positive consent, and even though he was the man in the situation he would still be on the receiving end. She merely gave his butt a playful pat, pulling her pants up and then pulled his back up and let him sleep off the drunk to prepare for the inevitable hangover he would receive the following day.</p><p>A day Andy wished he could forget. Boy did he have a hangover. He had hardly any recollection of the previous evening, especially giving drunken consent for Carol to play with his ass. As he took three Aleve and knocked back some Alka-Seltzer laden water and then laid in his dark room for a few hours, and then threw up the remaining contents of his stomach from an obvious touch of alcohol poisoning; the evening started to come back to him. He certainly remembered telling Carol all his sexual fantasies, which he was placated in remembering Carol's assurance it wasn't weird and that she herself was into weird stuff too. Andy of course wondered what those things meant and if their fetishes could comingle somehow. But of course, his heart belonged to Riley, who didn't know of his existence despite him having multiple pairs of her undergarments illegally procured from her domicile. Andy also remembered professing said love and devotion for the woman who didn't know he existed to the roommate he knew for a cool month or so.</p><p>Other than revealing his deepest and most kept secrets to Carol, the rest was a blur to him, though something in the back of his head triggered a sense that he missed out on something, especially considering that something was his apparently trans roommate was a shoelace away from ramming his ass with her cock. Either way, he knew this would probably come up in sober conversation at some point between the two. As much as Andy wanted to avoid Carol for all eternity to prevent such an inevitable event, this would probably be impossible. If anything, they did share a bathroom. That evening would produce such a meeting.</p><p>It was a Friday night. Andy hadn't seen Carol all day, mostly because he was sleeping off the worst and currently only hangover in his young life. He had just finished showering, and had the towel around him when he exited. Just across the hall was Carol's room, where her door was open and both roommates were in eyeshot. Carol was looking at herself in her mirror and touching up her makeup for an obvious night on the town. She turned, locking eyes with the boy. Carol was wearing tight booty shorts with a light blue and white striped T-shirt, with really red lipstick on her lips which she was touching upon.</p><p>"Andy, wait! Come here!"</p><p>Andy gulped. He knew this would lead to the conversation he spent all day dreading. He merely froze, racking his brain for an excuse, the obvious being: I'm naked. He only stammered. "It'll only take a second" she assured him.</p><p>"Uh, okay. Sure."</p><p>Andy walked in. Sure enough, Carol, still working on her face continued. "I've been thinking about what we talked about last night."</p><p>"Oh, right."</p><p>"Now don't deny it. It's okay, we live together, you don't have to be embarrassed" Carol urged him.</p><p>Now Andy was merely embarrassed because the secret was out and that their conversation was about to verge on the subject.</p><p>"Okay, so, what about it?" Andy asked a bit defensively, hoping to end it as quickly as it began and lock himself in his bedroom for the rest of his life.</p><p>"Drop the towel, I want to see you" Carol ordered him.</p><p>Now the blush was all over Andy's face. He certainly feared Carol would see his tiny dick and his spindly bod and then he'd really want to never leave his room, or move out as fast as he could and hope Carol wasn't so active on social media. But there was something commanding about Carol's voice which gave him a hard-on in the first place. Plus the cat was out of the bag as Andy's grown erection was tent-poling the towel wrapped around his waist to begin with. Nevertheless, he hesitated.</p><p>"Uh-uh-well—"</p><p>"Well come on, let me see" Carol insisted.</p><p>"Uh, why, exactly?" Andy asked the obvious but it was really to stall for time.</p><p>"Because I want to help you. You're sick of being a virgin, that's obvious, but I can sense you really want to act on your urges. You want to be a sissy. Maybe I can get you there."</p><p>"Oh, but, I—"</p><p>"No buts. Drop the towel, Andy. I won't ask again" Carol said, the second part much more stern than the first.</p><p>Andy gulped as Carol got up and moved towards him. Before she could reach out, Andy dropped the towel and his erection flopped free. Carol studied the boy's dick, barely five inches fully erect.</p><p>"Oh, this is perfect. May I?" she asked reaching a hand out. Andy nodded, but looked away. Carol reached and rubbed her fingers along Andy's dick, which throbbed as it happened. Andy reacted to Carol's cold fingers around his member. "Is it fully erect? And don't lie." Carol asked to Andy's very reluctant nod. "Then perfect. You're right, you do have a tiny penis, which is perfect because most dominatrix's love it when men's dicks are small, it helps them maintain control. Alright, turn around. Let me see your tush." Andy nodded and turned around. "Put your hands on the wall and stick your ass out for me."</p><p>Andy did as ordered and thrust his hips out so his roommate could inspect his rear, which Andy already knew he liked more than his penis anyhow. "You like?" Andy asked as Carol groped his cheeks and spread them apart.</p><p>"I love! You have a perfect sissy butt. And your asshole is so pink and untouched. You'll definitely make a Dom's day."</p><p>"Uh, thanks" Andy said sort of relieved.</p><p>Carol kept on stretching the boy's cheeks apart and she heard Andy make a tiny grunt. It was barely audible but she still heard it. Carol then knelt down so she was looking right Andy's ass and more importantly, his asshole.</p><p>"So, you've never done anything sexual before?" she asked.</p><p>"Never."</p><p>"Maybe I can change that."</p><p>"Really? A-Are you sure? I mean, we barely know each other" Andy said.</p><p>"You're so apprehensive. Last night you sounded like you were begging for some release" Carol reminded him.</p><p>"Yeah, but like, I never thought you'd ever-whoa!"</p><p>Andy was instantly quieted by Carol shoving her face into his asshole. She stuck her tongue right onto his hole which immediately puckered. Carol released her mouth and shot her tongue right on the center of Andy's virgin sphincter and swirled it around the rim.</p><p>"Ergh. Wow, that feels weird" Danny grunted.</p><p>Carol released. "You don't like?" she asked.</p><p>"No-no, I do, it's just weird."</p><p>"You're a virgin sweetie, it's all gonna feel weird at first."</p><p>Carol then right back to work, spreading Andy's cheeks out and then shooting her tongue right onto his asshole, swirling it around and letting her saliva leak down his crack and fall onto his ball sack. She got her tongue to try and open up Andy's asshole and shot it inside the boy's previously untapped sphincter. Andy's light grunts turned into moans while Carol tongue-fucked his asshole.</p><p>"Wow, okay that feels good" Andy moaned.</p><p>Carol was satisfied, but continued. Her tongue was trying to force it's way inside of Andy, while her hands stretched his cheeks out wide to accommodate her head being betwixt his crack. Andy could feel an arousal below the belt from getting a rimjob. His dick was starting to rise. He reached a quivering hand down to his crotch and grabbed his little dick and stroked it wildly to the tune of Carol rimming his ass.</p><p>Carol wished she could jerk off too. Her dick was confined in her pants but she definitely wanted it to flop free and shove it up Andy's lubed up asshole. She wanted to wait though, figuring there would be a better time to truly take Andy's butt cherry, especially if he begged for it.</p><p>"Please don't stop" Andy begged,</p><p>He continued to jerk himself off and could already feel like he was getting close. Damn. He never figured his first sexual experience would be getting his butthole licked but then again, he never thought he'd have a sexual experience to begin with. He could feel the warm pre-cum leaking onto his jerk-off hand.</p><p>"I'm…getting close" he moaned.</p><p>Carol got off of his ass. "Cum on my face."</p><p>"What?"</p><p>"Now! Don't waste it on the wall!"</p><p>Andy quickly did an about face and turned his small wang onto Carol's cute mug. After some more furious jerking off coupled with Carol fondling his balls, Andy shot a big load onto Carol's face. Then another, then the last shot dripped down onto her mouth. Andy gave one last moan as he the last few drops of cream fell onto Carol's mouth.</p><p>"Whoa" was all the boy could say.</p><p>"You like?"</p><p>"Hell yes."</p><p>"Good. Cause this face could be yours. Now lick it off."</p><p>"What?" Andy asked, confused by both parts of that sentence.</p><p>"Lick your cum off my face" Carol ordered.</p><p>"Uh-uh—"</p><p>"Now, Andy."</p><p>Andy complied. He got down on his knees to face Carol. After a brief hesitation and not wanting to piss off the supposedly sweet roommate, Andy went right in and gave a big long lick onto the side of Carol's face, licking up his second shot of cum. Andy winced as he forced down the salty mucus taste. Carol raised an eyebrow, as she assumed he was finished. Andy went back in and licked more and more of the cum off of her face, also getting the powdery makeup with it as well. Then Carol opened her mouth and with some cum on her tongue, shot it into Andy's mouth, snowballing him. Andy savored the kiss though, as this was also the first real kiss he ever had. Eventually, after the two got their tongue's acquainted with one another, Carol released.</p><p>"Good boy. In the future, don't hesitate, unless you want to be punished." Carol ordered, helping herself and Andy up. "Okay, I need to fix my makeup then I have a date to get to, make sure you're home tomorrow afternoon, I'll have something or you" Carol explained.</p><p>Andy, still very naked raised an eyebrow.</p><p>"Uh, okay"</p><p>"You're still here? Go, I've dismissed you" Carol ordered.</p><p>"Oh, right. Sorry" Andy gathered up his towel and headed out.</p><p>Andy was mildly weirded out from the whole affair. While it sort of fit in with his fetish he definitely never thought he would cum from getting his asshole licked. Plus he was also confused about Carol ordering him to lick his own juices off of her face. But, despite any reservations he was having, it was obvious it wouldn't be the last encounter between the two and Andy felt as though he was up for anything, or was at least desperate for anything.</p><p>He was mostly eagerly awaiting the next day and whatever thing Carol had waiting for him, which he hoped would be some kind of sexual intercourse. He was also very intrigued by the sternness in Carol's voice directing him what to do. He thought maybe Carol was interested in the dominatrix lifestyle like Riley was…</p><p>Oh right, Riley.</p><p>Andy face palmed. He really wanted his first time to be with her. He always imagined it would involve her spanking his ass before bending him over and ramming one of her strap-ons up his butt before he would get to cum. Maybe if he were lucky, he could get inside her pussy, too. He didn't want to count Riley out but it was obvious that he couldn't turn down free sex with his own hot roommate now. Andy had waited far too long for this opportunity to slip right by him, plus, it's not like Riley was clamoring to fuck him, anyway. Hell, she barely knew he even existed. He still wasn't going to write her off just yet. There was no question Andy lacked confidence, which was about all that stopped him from propositioning Riley to fuck him.</p><p>Anyway, the next morning came and went. Andy woke up to see Carol wasn't around at all. The afternoon approached and Danny waited, while watching something pointless on Netflix. Finally, Carol arrived home with several bags under her arms, as well as pushing a very large brown box.</p><p>"Hey" Andy said.</p><p>"Oh good, you're home" Carol went right over to the couch. "Take your pants off" she ordered.</p><p>Andy was hoping she would say that. He took off his shorts and underwear too, and his dick flopped free, getting hard from Carol's orders.</p><p>She reached into the back and pulled out a small plastic device wrapped in packaging. Carol quickly discarded the material and the plastic wrap. Andy studied it. He knew what it was though, it was a cock cage. This one was colored in pink and came with its own keys.</p><p>"A cock cage?" Andy asked. "For me?"</p><p>"Yes. If you want to be a sissy slut, sissy sluts wear cock cages, because you need the permission of your mistress to cum. From now on, you'll orgasm at her discretion. Now spread your legs" Carol ordered.</p><p>Andy did as told while Carol opened up the cage and finagled his tiny dick inside of it, locking it into place with his balls, and closing the lock. Andy blushed as his cock now had no room to grow, but it was such a turn on for him.</p><p>"Now it has a hole so you can still pee if that's what you're thinking" Carol said before standing up. She got something out of another bag and opened it from the box. It was a pink vibrator with the words: SLUT written on the shaft. "Now then, we need to train your pussy to start taking dick. You're a virgin so you need all the help you can get."</p><p>"Pussy?" Andy asked in disbelief.</p><p>"Yes, you are a sissy slut now, Andy. You don't have an asshole, you have a pussy, and pussies get fucked."</p><p>She took out from the bag a bottle of lubricant and without wasting any time drizzled some on the cock and on her fingers. Andy kept his legs spread while a huge amount of blush overtook his face. "Good girl" Carol said. "You're already ahead of me, that's good."</p><p>Carol took her lubed up fingers before bending her head down to rim Andy's ass once more, and stuck a finger inside his hole without warning. Andy gave a deep breath, this was the first time anything was put up there. Carol wasted no time with a second finger.</p><p>Andy wished he could get hard. Unfortunately he couldn't and the very thought of being anally fingered really turned him on, especially Carol calling him a slut. He held his thighs back while Carol continued to shove her digits inside of him.</p><p>"That feel good?"</p><p>"Oh yeah! So good."</p><p>"Good" Carol smiled.</p><p>She removed her fingers and moved the vibrator into place, slowly inserting it inch by inch. Andy wasn't used to this much inside of him at once…and he wasn't used to anything until a few moments ago, so this took time for his sphincter to subside and accept the dildo being slid inside of him. Carol watched it enter his hole and she became hard under her pants, hoping for her own ego to subside and she succumbs to her own urges and fuck Andy with her dick.</p><p>Andy's cock throbbed, still locked in the cage. He could feel it get tight while locked in place, wishing it could get hard, but it was no use. Andy moaned while Carol managed to get the entire dick up his ass. She twisted the cap and turned on the vibrating feature and Andy was instantly overcome with pleasure.</p><p>"Whoa!"</p><p>"Oh yeah, that's the best part" Carol chuckled.</p><p>"Oh yeah, oh…yeah!" Andy moaned.</p><p>"Now I want to see you train yourself with this at least once a day, okay Andy?"</p><p>"Yes, of course."</p><p>"Good, we need your ass to be able to accept cocks on command. Nobody likes a shy anus" she ordered him.</p><p>Andy nodded as he could barely hold up his legs from the vibrating rush of euphoria being sent from his rectum up his spine. He managed to get a grip once more as he felt some lube drip from his ass and onto the side of the couch.</p><p>"Also, we need to find you a new name. Andy sounds too masculine, you need a girly name that perfectly fits your slutty persona" Carol insisted.</p><p>Andy grunted. "Okay. What did you…have in mind?"</p><p>"I was thinking about something like…maybe Bianca? How does that sound?" she asked</p><p>Andy's cheeks immediately lit up. That did sound good to him. "I like that!"</p><p>"Good, then you're Bianca now. My new sissy slut" Carol chirped.</p><p>She shoved the entirety of the dildo inside of Bianca—er, I mean, Andy's ass, nearly getting the twisting black base inside of him. Andy gritted his teeth and blushed a dark shade of pink. Carol smiled as she left it inside of him for what seemed like an eternity.</p><p>"I bet you wanna cum, don't you?" Carol asked.</p><p>"Hell yeah!"</p><p>"Sorry, not without my permission. When I feel like it Bianca, you may cum."</p><p>"Please Carol!"</p><p>Carol rammed it into his ass again. "That's another thing. I'm not Carol anymore. I'm Mistress Carol, or simply Mistress. Got it?"</p><p>"Please Mistress. Please let me cum?" Andy begged.</p><p>"Nope, not quite, slut."</p><p>Carol made a few more thrusts into Andy's butt before sliding the dildo out. Andy wishing he could just cum, but it was no use. Carol was a bit sweaty from all the exertion, and she stood up, towering over the sitting Andy.</p><p>"Alright, tomorrow I got a special surprise for you, which I will be making in my room, do not, and I mean DO NOT bother me until I request you, understand Bianca?" he nodded effusively. "Good" she gave him a kiss on the forehead. "You're doing a good job" she then pushed the box into her room, leaving Andy with the vibrator, which he immediately shoved up his ass once more.</p><p>Later, Andy lurked outside Carol's closed door, wondering exactly what it was she was making for him. But he knew he'd figure it out once she sent for him. He was sort of liking Carol being this dominant presence over him, already locking his cock and helping him train his ass. It was what he really always wanted…</p><p>…Except, once again, Riley was the fly in the ointment. Andy really wished it was Riley doing all this to him, but alas, it was his even hotter roommate. But Andy figured, now that his cock was locked up, maybe this could be a new conversation starter between the two of them? After all, he knew Riley loved to dominate men, and now he had an in to talk with her.</p><p>He spent all night thinking about it. He held the dildo in his hands while he laid in bed, with one hand, playing with his caged dick. He figured he could go some time tomorrow and just knock on her door, and if not a pity fuck, maybe they could just talk.</p><p>The next day, he got his chance. Carol was in her room all day, so Andy took the opportunity and walked out, dildo in hand over to his neighbor's apartment. He stood outside Riley's door as if this task was impossible to do. He made a fist and held it out as if he were about to knock, but he just didn't have the strength to do so. Something inside of Andy was making him puss out of this opportunity. He thought this might have something to do with feeling guilty about Carol, just going and wanting to be fucked by another woman. It wasn't like the two were in a relationship or anything real but it just didn't feel right. Andy just simply didn't have the confidence.</p><p>Meanwhile, inside, Carol finally emerged from her room with a few pairs of panties and barged into Andy's room, first realizing he wasn't there. "Bianca, I'm almost ready for you. I got you a pair of panties to wear…Hello? Andy?"</p><p>She shrugged, realizing Andy wasn't in his room, and simply opened up the top drawer in his dresser to put the panties inside. Of course as she did, she got a bit perplexed. That drawer was where Andy hid the corset, stockings, and pair of panties he stole from Riley's apartment. Carol smiled as she picked the pink lacey pair. "You naughty bitch." Hatching an idea, she took them from his dresser.</p><p>Outside, Andy gave up and walked back towards his apartment. He closed the door and se the dildo aside. He heard Carol call from her room. "Is that you, Bianca?"</p><p>"Yeah, mistress."</p><p>"Good. I'm ready for you. Take off your clothes and come into my room."</p><p>Andy gulped as his heart started beating a million miles a minute. He made quick use of stripping away his clothing, his caged cock flopping free from his shorts. He took a deep breath and slowly walked over into Carol's room down the hall.</p><p>Of course when he entered, Andy noticed a few things. For one, there was a giant metal contraption on a machine jutting off of Carol's bed with a long extended metal arm and a long dildo attached to it…</p><p>…And then of course there was the corset, panties, and stockings all laid out neatly on Carol's bed. She raised an eyebrow as Andy blushed. He had on a perfect 'oh shit' face. He then realized he should have hid his things better not once thinking Carol had no business in his room unannounced.</p><p>"When were you going to tell me about this you dirty little slut?"</p><p>"Um, you never asked?" Andy said nervously.</p><p>"Wrong answer. When did you get these, hmm? I figured since you were into this you would have told me by now."</p><p>"Well…" he couldn't lie. "I may have…borrowed them, from our neighbor. The one I was telling you about."</p><p>"Really? Does she know about this?"</p><p>"No, she doesn't."</p><p>"Then you stole them?"</p><p>"Technically…yeah" he sighed, defeated.</p><p>"Well, then that makes todays training all the more fun for me. Get over here, whore. You wanna be treated like a slut, you're gonna dress like a slut!"</p><p>Carol walked over to an apprehensive Andy and pulled him over to her bed. She quickly started to bend him over and laid hard smacks on his ass cheeks, which clenched up with each passing smack.</p><p>"That's naughty, Bianca! Dirty girl!"</p><p>She continued to spank Andy until his cheeks were red. Then she took the panties and forced them through his legs and over his ass. She spanked his cheeks a little bit more while she did this. Then she took the fishnet stockings and slid his feet through and up to his skinny thighs, which filled out nicely.</p><p>"Dirty little bitch. It's okay, I'll straighten you out" Carol sternly assured him.</p><p>She then took the corset and put it around Andy's mid-section, pulling the laces closed and forcing him to suck in before tying the laces in place. "There now you look like a little sissy cock-sucker already. Now, let me show you to this" she motioned to the contraption. "This is a mechanical dildo machine. It will electronically make this dick move forward and it will literally fuck you until I turn it off. This is going to help properly train your ass in addition to your vibrator. And I can't think of a better time to test it out" Carol explained. "Now, hop on my bed, on all fours, and spread your ass in front of the dildo!"</p><p>"Yes, Mistress Carol."</p><p>Andy uncomfortably hopped onto the bed and finagled his ass over toe dick. He moved the thong part of the panties aside to accommodate it, with his sphincter lined up and ready to be fucked by the dildo. Carol drizzled lube onto the dick and shoved two fingers right into Andy's ass to help stretch him out.</p><p>She then wasted no time before turning on the machine, helping to guile it as it slowly thrusted inside of Andy's sphincter, stretching out his sissy rectum. "Good girl, Bianca."</p><p>Carol watched the machine split Andy's cheeks. He pushed himself back more into the machine to get it to go deeper. He grunted as it fucked him, his cock wishing it could spring from the cage so he could stroke it. No use.</p><p>"Oh fuck, oh yeah!" Andy moaned.</p><p>"Increase the sound of your voice. Doms are fucking sissies, not men."</p><p>"Oh yeah, oh yes!" Andy yelped in a higher pitch.</p><p>"Good!"</p><p>Carol then hopped on her bed, and towered over Andy. She smirked before turning around and started to lower her pants and panties, revealing her giant tushy. Andy stood in awe as this massive booty was shaking right in front of his face. Carol stopped her pants right below her cheeks, obviously to hide the fact that below her asshole wasn't a pussy. Carol used her hands, and in front of her pulled out her flaccid started to stroke herself, while her booty was in Andy's face.</p><p>"Well, what are you waiting for slut?" Carol asked. "Lick my asshole! The way I licked yours!" she commanded.</p><p>Andy immediately shoved his face into Carol's crack and shot his tongue out, licking her hole. Had he looked a little lower, he'd notice in fact she wasn't packing a pussy below that ass, but he was in too much pleasure to notice.</p><p>"Oh yes Bianca" Carol cooed. "Lick my asshole. Cause I got a real big surprise waiting for you once you're done" she snickered evilly.</p><p>Andy felt that ominous, but didn't care, and savored the rim of Carol's seemingly perfect asshole. He stretched her cheeks out wider and swirled his tongue all along the outside of her hole.</p><p>"Yes, you're such a good ass-licker, Bianca. I hope you're good at sucking cock, too."</p><p>Andy wanted to live up to that compliment and spread her cheeks as wide as he could, shoving his tongue into Carol's asshole. He licked and kissed her hole while moving his face away briefly and watched it pucker. Finally, Carol moved a step forward.</p><p>"Okay, Bianca, are you ready for my dick?"</p><p>"Oh yeah. Strap it on, mistress."</p><p>Carol chuckled. "Oh no, there's no need for that" Carol immediately turned around and practically slapped Andy's face with her cock as she did. "It's already here."</p><p>Andy got cross-eyed as he eyed down the nine inch veiny dick right in front of his face. Huh, he never even would have given it a second thought. But it made sense why Carol answered his add to begin with…</p><p>"Y-Y-You want me to suck-suck—"</p><p>"Quit stammering, slut. You're my sissy now. Good sissies don't ask questions, they suck cock. Now be a good girl and chug my tranny dick!"</p><p>Andy nodded and opened his mouth while Carol immediately shoved her cock into his mouth. Andy's stretched asshole puckered from the impact and he blushed from this new experience of having both his holes filled. Andy coughed and spit her cock out, some tears fell down his face.</p><p>Carol's dick was dripping in saliva. "You'll get used to it, now put it back in there, slutty whore!"</p><p>Carol shoved her dick inside of his mouth again and was slower this time so Andy could get used to the idea of deepthroating a dick. After a few thrusts in and out, Carol managed to get most of her length inside of his mouth.</p><p>Andy choked down her cock, his gag reflex kicking in once again, but he quickly played through the pain and continued to suck down her massive member. He took this time now to think while Carol took a hand and shoved the back of his head onto her penis.</p><p>He didn't mind this new experience so much. Sure, it was humiliating to be fucked by this dildo machine with his cock locked up and sucking his apparently trans roommates dick simultaneously, but it was such a turn-on. This was what Andy was looking for this entire time.</p><p>"Get used to this, Bianca" Carol cooed. "I want you to suck my cock every day. And were gonna train your little whore ass until you're able to take it. You're gonna be my little anal sissy, just like you've always wanted, right?" With his mouth full of her dick, Andy nodded, and got back to work. Now using a free hand to jerk her off while he sucked. "Soon, I'm gonna use this cock to stretch your pussy out every day. You're gonna be filled with tranny cum until you're pregnant!" she joked.</p><p>Her own words were making her close. Carol could feel her cock throb from being stroked and sucked by Andy. Carol looked down at her little obedient twenty year old slut, thinking of the things she wanted to do to him.</p><p>"I can't wait" she cooed. "I want to get you a tattoo on your slutty ass, Bianca…something that really says you're mine, slut."</p><p>She looked down and watched the machine continuously pound his ass from behind. She was ready to fire. Andy was really blushing, now thinking of essentially having a brand on his ass permanently cementing his sissy status with Carol. But he felt her dick throb, and knew a climax had to be imminent.</p><p>"Oh yeah! Oh baby, I'm close!" Carol quickly pulled her dick out of Andy's mouth and looked at his teary eyed face. She stroked herself while Andy stuck out his tongue. With one last moan, Carol shot her load. Hot, sticky ropes of cum blasted onto Andy's hair, his cheeks, below his eyes, on his nose and a few last drops dripping onto his tongue. When she was finally finished, Andy swallowed the cum on his tongue and licked his lips. The two stared up at one another, satisfied.</p><p>Carol knelt down and smothered Andy's face with her tits, wiping her own cum off of his face with her bosom. Andy motor boated her for a few moments before Carol got down and stopped the machine. Andy pushed his ass off of it, and collapsed on the bed.</p><p>"Alright, slut. I'll call you tomorrow when I'm ready for you. I'll have something else for you to wear for tomorrow's lesson. Now get out of her. Clean yourself up!"</p><p>"Yes mistress" Andy obeyed, and left.</p><p>He was so horny. He ran into the living room and fell to the floor, so frustrated he couldn't cum. He grabbed his dildo and bent down on all fours, shoving it into his gaping asshole while using his free hand to shove a few fingers in his mouth, thinking about everything that just transpired, and thinking about getting his ass tatted up.</p><p>The next day, Andy woke up and didn't see Carol at all. He thought about last night, not minding one bit she never told him she was trans. It was kind of hot, that surprise turnaround revealing her dick made Andy want to cum in his pants just thinking about it.</p><p>He liked the idea of being used. This new Bianca persona really encapsulated who Andy really wanted to be but never knew it: a submissive sissy bottom slut. Now he really had something to tell Riley. He knew he had to at this point, even if it was in passing. He went into the living room where on the couch he noticed a few things and blushed when he saw them. It was some makeup, with a frilly black v-neck blouse with long black and white striped skin-tight sleeves. The blouse ended in a midriff. There was also a pair of panties with a heart sewn out in the middle, making them look more like an elaborate jock strap. Then there was a very short black frilly skirt and a pair of silk black and white striped stockings with a pair of high heels. And to top it all off, a long black haired wig. There was a note with all this.</p><p>Bianca,</p><p>Have all this on and ready when I get home, today is your first day as a sissy slut. You need to dress like one. Don't keep me waiting,</p><p>-Mistress Carol.</p><p>Andy then thought for a moment. And it hit him: THIS was how he was going to talk to Riley! She wasn't going to fuck Andy…she was going to fuck Bianca, a sissy slut whose new in town and looking to be rammed.</p><p>Andy smiled and got right to work. He watched a few makeup tutorials on YouTube on how to apply makeup, then he dressed himself up, but he wore the pair of her panties. Andy finally looked at himself in the mirror, and he looked like a perfectly passable girl.</p><p>He ran outside and with no hesitation, he knocked on Riley's door. After a few moments, the tired Latina in a t-shirt and pajama pants opened the door, and raised a very questionable eyebrow.</p><p>"Can I help you?" she asked.</p><p>"Hi, I'm Bianca. I was stopping by because I had something to show you" Andy said in the girliest voice he could muster. He lifted up hi skirt and pulled down the panties revealing his caged dick. "These panties wouldn't be yours by chance, would they?"</p>
  </div></div>
<a name="section0002"><h2>2. Missed Opportunity</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Summary for the Chapter:</b><blockquote class="userstuff">
            <p>Andy gains new confidence as Bianca, his new sissy persona, he attempts to "return" the stolen panties to Riley who angrily rebuffs him, sending him away with threats and no cocks while taking her thing back, but Riley may have spoken too soon, while she listens in on Carol fucking Andy's brains out with the dildo machine, Riley wishes it was her fucking him instead.</p>
          </blockquote></div><div class="userstuff module">
    
    <p>We pick up right where we left off. Andy, now dressed in drag stared at his dominatrix crush Riley, who was very perturbed to say the least at this boy exposing himself to her in front of her apartment door, technically in public.</p><p>We'll backtrack quickly on Andy's outfit. It consisted of a frilly black midriff, with detached skin tight black and white striped arm stockings, a very short frilly black skirt, black and white striped stockings, and black high heels. Rounding out his look was some makeup and a long black wig, perfectly covering up his short haircut. He of course had on a stolen pair of Riley's panties which were now pulled down to expose his cock, locked in a cock cage.</p><p>Riley was not surprisingly mesmerized at the sight in front of her. This was quite possibly the last thing she expected to see knocking at her door. Despite her being a dominatrix who relishes in this sort of thing, she was nonetheless disturbed that this crossdresser...or was it a trans person? Andy was so passable Riley couldn't tell, but anyway she was disturbed by the fact that Andy merely stood there exposing himself completely unannounced.</p><p>With a quick kneejerk reaction, Riley pulled him inside. "W-What? What—what—who are you, come inside before the fucking cops get called, Jesus!" she looked to see if anyone noticed, they didn't; and she slammed the door behind her.</p><p>"What the fuck is wrong with you—who are you?" she asked.</p><p>"I'm Bianca" Andy retorted.</p><p>"Yeah-yeah I heard you. What's your real name?"</p><p>"I told you, Bianca" he retorted.</p><p>Riley rolled her eyes. The twenty-three year old did not need nor want this, especially considering Andy seemed to be this weird sissy robot she didn't ask for. Yet, still, she was nonetheless intrigued that someone would go to all this trouble to just brazenly show up at her doorstep practically begging for a pity fuck. Part of Riley wanted to usher Andy out as fast as he came in, but part of her wanted to learn more. All in the same she put on the tough girl card.</p><p>"Fine, "Bianca", what do you want? And why are you here?"</p><p>"Like I said, I was wondering if these panties are yours?"</p><p>"I mean..." she trailed, shrugging in frustration. "I mean they look like they could be—I dunno man, I have a lot of underwear and I'm lazy as fuck, are they mine or not?"</p><p>Andy was a bit disappointed that Riley wasn't joining in his little game but remained in character. "They are."</p><p>Riley wasn't exactly disturbed that he was wearing them or how he got them, it just felt weird to her. "Okay, did I lose them in the laundry room, and you're being a little fucking creep trying to return them? What's going on here?"</p><p>"I stole them, from your room" Andy explained, putting his hands behind his back and raising his toes in the heels.</p><p>Riley did a face palm. This is what she gets for never locking her door and then living a life outside of it. That would explain why her messy room seemed to be even messier upon her returning from wherever, but she went from disturbed to angry upon hearing this revelation; that this stranger stole from her.</p><p>"What the fuck?" she asked. "Why did you steal my panties?"</p><p>"Cause I'm naughty" Andy chuckled.</p><p>Riley didn't like that answer. Hot, steamy, dominatrix Riley wasn't in the room right now. Broke, annoyed, tax paying Riley had entered and she was in a face-punching mood and not so much a spanking, face-sitting kind of mood. She lunged and pinned Andy against the nearest wall.</p><p>"Listen to me you little fucking shit. Clearly you can tell I can kick your ass into oblivion, so I am going to give you one time to—"</p><p>"I stole a corset of yours too, and some stockings" Andy mused.</p><p>Riley raised an eyebrow. "What the fuck? My good corset? No wonder I couldn't find the damn thing. W-What is wrong with you? And give me some answers I'm sick of your little sissy routine!"</p><p>Andy sighed and got out of Riley's grip and danced around the apartment, leaving Riley a bit dumbfounded at his bold attitude. "Oh Riley, you're such a tough little minx. Why spoil your anger by pounding my face in when you can get the strap-on I know you have and pound my ass in" Andy cooed, bending over a crappy couch in Riley's living room, exposing his ass.</p><p>Riley rubbed her temples, clearly being tough wasn't working. She needed a different approach, and maybe sexually punishing this Bianca would give her the boost she needed that week, she had been known to fuck feminized guys many a times before.</p><p>For Andy's part he was really getting into this. Regular Andy was a total pussy and didn't even have the courage to talk to Riley in any capacity, let alone talk and dance his way out her kicking his ass.</p><p>Riley approached Andy in a very precarious position bent over her couch. She got a good view of his ass while her panties were underneath his cheeks. She blushed a little bit, he had such feminine hips for a guy.</p><p>But as much as Riley wanted something to become of this, she knew how to win over the hearts of her men...by getting them off on HER terms, and not there's. She stopped herself short from gripping onto Andy's cheeks, and instead pulled him up by his wig, which he did a very good job of securing.</p><p>"Yeah, I don't think so!"</p><p>Riley used a free hand to yank her panties down and Andy stepped out of them, obviously knowing where this was going. His plan seemed like it wasn't going over the way he wanted it to go. Maybe Riley wasn't as easy as he first thought?</p><p>"Where are my other things?" she demanded, pulling the wig harder. Andy did such a good job securing it, that it was actually hurting him to be woman-handled like this...but he was kind of turned on by it, once he got past the pain that is. "Where. Are. They?" Riley demanded again.</p><p>"Erm—m-my apartment" Andy wheezed, forcing himself to stay in character.</p><p>"Well then you'd better direct me. Let's go, bitch." She sneered.</p><p>Riley led Andy to the door and the two ventured outside into the sweltering San Fernando Valley heat. "Which way?" Andy pointed to the door across the hall. Riley dragged him over and she opened up the door. She figured the set-up was similar to her own apartment and walked through the living room/foyer/kitchen and down the hallway towards the two bedrooms. She first came to Carol's room, Andy's roommate and current shemale mistress.</p><p>"This your room?" Riley asked, pointing to the dildo machine that destroyed Andy's ass the previous evening.</p><p>"N-no" Andy huffed. "My mistress's, actually."</p><p>"Whoop-dee-fucking-do. Now where's my fucking shit?"</p><p>"My room" Andy pointed to his room next door.</p><p>Riley dragged Andy inside and threw him onto his bed, and started to rifle through his drawers, assuming that would be where he would keep them. She tore all his clothes out, and slowly started to find what she was looking for.</p><p>Andy was down, but he wasn't out. "You know, maybe if you stayed behind you can watch her train me today."</p><p>"Yeah, well maybe she can train you to be a better thief—ah, this looks right" Riley had found her stockings. "Where's my corset?"</p><p>Andy pointed to his hamper. Riley again threw out whatever wasn't hers until she found the corset. She made a slight smile, satisfied she had the things back that she never would have noticed missing had Andy not said anything. She leapt onto the bed and straddled the sissy boy sticking a finger in his face. "So help me, if I even think you've stolen anything of mine again—or if you so much as set one foot in my place unannounced, you can forget the cops, I'll just kill you. Got it!?" she demanded.</p><p>Andy liked the force in her voice, but he knew she wasn't joking, which admittedly scared the living hell out of him. So he forced. A nod and an innocent smile while Riley grinned, smacking his cheek and getting off of him. "Yes ma'am."</p><p>"Good." She headed for his door.</p><p>"I'm sure she wants to punish me. Is that something you might be interested in?" A desperate Andy asked.</p><p>Riley stopped in the doorway. She was interested, in fact she was interested in getting out her strap-on and fucking Andy's ass right then and there, but she still had principles and she didn't want Andy to win, considering she had the brains to realize this was part of some weird and perverse plan of his...which it was.</p><p>"How do you know what I like, exactly?" she asked.</p><p>"I can hear you. Our walls aren't exactly thick."</p><p>Riley rolled her eyes. "Well, I guess I can't blame you for hearing" She sighed, she looked at the cute innocent sissy sitting so obediently on his bed, like a long lost puppy in need of some love. But Riley believed in tough love, and more to the point, she barely knew Andy, hell she didn't even know what he looked like without the girly clothes and makeup.</p><p>"There are a million ways you could have introduced yourself to me. But you steal from me and just assume that you can tug at my perversions that I'll just be putty in your hands? Fuck you" she stomped away, leaving Andy in a mess of his own sexually frustrated pomposity.</p><p>He laid back down on the bed and heard the front door open and slam shut just a few moments later. Andy felt depressed. He slumped out of bed and looked at himself in the mirror, his makeup was running from getting misty eyed from being woman-handled, but more so from his plan ultimately failing. He took up the makeup kit and reapplied some of it, knowing Carol would be very angry if he didn't look perfect, he had already fucked one potential relationship, he wasn't about to ruin two in a single day, that would be a new record to his already pathetic love life.</p><p>Riley stomped back to her apartment, slamming the door shut, while locking the deadbolt and the chain lock, as if to say she was never leaving her door unlocked again. She marched to her messy room and lazily dropped the contents she carried right back to their previous place before Andy had stolen them...and washed them, and folded them.</p><p>She slopped onto her bed and crossed her arms. Like many people with weird sexual desires, Riley didn't have a group of friends she could vent to about these recent events. Other than the men she humiliated and fucked, it was her secret alone...and apparently Andy's and anyone else in her apartment complex within earshot. Imagine a split screen now with Andy and Riley laying on their beds. Their meet-cute was more like a meet-ugly, an utter failure. All Andy could think about what a screw-up he was and that he couldn't do the one thing he enjoyed in life correctly, a sad state of affairs in a bevy of ways.</p><p>Riley on the other hand was starting to think of the missed opportunities. She knew every way to punish a man, even to ways that would only sexually benefit her, she knew just how she could have gotten revenge on Andy but she stuck to her guns. She liked to get to know her clients before fucking them and in reality she was just taken off guard by Andy's random boldness and his fast and loose petty theft of her things.</p><p>"Fuck" she turned and screamed into a nearby pillow. "Fuck! I can't believe I just did that! God that little fuck was such a cutie! Grrrrr!" She kicked her feet, then screamed into the pillow again. "Why do I always get the weird ones!?" she moaned.</p><p>She sighed. She was a twenty-something with more problems than letting a possibly sexy romp slip through her fingers. Riley laid there for a few moments. Maybe she was being too harsh on Andy? To be fair, grabbing him by the hair was a suitable punishment instead of filing a police report, but maybe she went too far?</p><p>After all, what did he steal? Three articles of clothing she barely realized were missing until he pointed it out? And he looked so hot in drag. She wondered a little bit what Andy looked like without it on? Which then made her believe why she never noticed him before because he probably looked ordinary, cause he did.</p><p>Whether it was her urges calling her, as Riley was getting warm and moist underneath her panties or a need to try to be a better person Riley got up, and walked over to her equally disgusting bathroom and briefly fixed her hair.</p><p>She headed for the front door and unlocked it. She opened it up but quickly closed it when she saw someone across the hall going into Andy's apartment. She opened it just a crack. It was a woman, several year solder than her, with platinum blonde hair, hour glass frame with plump features, namely big tits, and a massive butt, Andy's roommate/trans mistress: Carol Larzaretta. She carried with her several bags along with a tote bag. She walked inside, and closed the door behind her and Riley heard the deadbolt turn. She sighed, figuring this was definitely a missed opportunity, and closed the door in defeat. Little did Andy know, that while it looked like he had lost the battle, the war had just begun, and his odds were starting to look kind of good.</p><p>Inside Andy and Carol's apartment, Carol tossed the bags aside and summoned her sissy. "Bianca? I'm home!" she called like Ricky to Lucy.</p><p>Andy, still dressed like a slut stumbled into the living room. "Car—Mistress, you're home early" he blurted, breathing a sigh of relief that nothing had happened with him and Riley as Carol would have seen it.</p><p>"Yeah, I clocked out early and thought I'd get us a few things, but look at you" she chirped. "I guessed your size but I had no idea you would fill this outfit out so well. You look like such a little sissy slut. How do you feel?"</p><p>Admittedly lousy, except for the fact Carol probably would have punished him hard if she ever found out he tried to bottom to Riley. But, a part of him wanted her to find out, maybe she would punish the two of them...or maybe Riley would turn the tables and punish him and Carol...actually, the possibilities seemed endless, but Andy figured the Riley ship was sailing fast and he had to save face for his bubbly mistress.</p><p>"I feel fantastic" Andy beamed in the fakest girliest voice his depression could muster.</p><p>"Good" Carol approached the sissy boy and rubbed his cheek. Andy was afraid he had a tell and Carol would have discovered that he went over to Riley's without permission asking her to fuck him.</p><p>In a way he was wondering what the harm actually was? He made it sort of clear in his drunken moment with Carol that his heart belonged to Riley and that Carol's goal was to train him to be a sissy, so what strings were attached, exactly?</p><p>Then again, he wasn't fully aware of Carol's terms of his new role. Was he allowed to ask strange and lazy dominatrix's to fuck him or did he have to ask Carol's permission first...if such a privilege would even be afforded to him.</p><p>Fortunately, Andy kept a straight face while Carol smiled, his ruse apparently working. "Come with me, Bianca. It's time for the days training" she ushered him into her room, carrying two of her bags with her.</p><p>She sat down on her bed while Andy obediently stood at attention with his arms behind his back. Carol slapped her lap and Andy figured correctly that was his cue to get over her knee. He plopped down and leaned forward, his ass sticking up in the air, the skirt only covered it partially at this angle, but Carol flipped it up. She rubbed his hairless ass down.</p><p>"Such a cute little tushy" she licked her lips. "Have you been training yourself with your vibrator?" Carol sternly asked him.</p><p>"Yes, Mistress."</p><p>"Good. Soon I want you to be able to take my dick in your tight little ass, but for now I think I'm gonna spank it" Carol raised her hand and without warning, came down hard on Andy's ass. He yipped. "You're a bad little sissy bitch, Bianca. Bad little bitches get spanked on their hot asses, understand?"</p><p>Andy nodded. "Y-Y-Y-Yes, m-mi-mi-m-mistress."</p><p>Carol raised her hand again and slapped Andy's cheeks, and his legs writhed from the pain. Carol made a few more slaps to his rear in slow intervals at first before picking up the pace and simply walloped his cheeks.</p><p>Andy winced as he could feel his ass reddening from Carol's strangely strong hands coming down hard on him. He felt tears forming in his eyes. At first he thought this was from the spanking, but in reality, it was from the missed opportunity with Riley. This being his one true chance with a newly found confidence to casually ask to fuck, and it failed spectacularly.</p><p>Carol stopped a moment to grope Andy's cheeks, spreading his pink melons apart and watched his formerly virgin asshole pucker. She let some saliva fall out of her mouth and it landed on his bullseye. She used one hand to continue to spank his cheeks one at a time while using her free hand to finger inside of him with her middle finger as if to say "fuck you, you're mine."</p><p>This of course was quite loud, and with their very thin walls it was attracting attention...certain attention. Riley was back in her bedroom laying on her mess of a bed. After perusing TikTok for several joyless minutes she started to hear the faint yet familiar sounds of hands coming down on skin...hard, something she was used to doing.</p><p>This was followed by the sound of high pitched feminine moans. Riley turned off her phone and was dead silent. Andy was right, there walls were paper thin. 'Is that what they hear?' Riley thought to herself.</p><p>She could hear Carol ordering "Bianca" to stop being such a little bitch while continuing to finger and spank his cheeks. Riley groaned, shoving a pillow on her face. In frustration she threw it off, completely disappointed of her missed opportunity to fuck this seemingly new sissy in town. If only she didn't want to punish him by cock-blocking him, which was now ironically being more of a punishment to Riley than Andy, at least he was gonna get some dick while she just laid there, alone.</p><p>But the sounds...they were so...hot. Riley bit her lower lip as she shut her eyes thinking about the sex scene that might have been. She tore her pants off and shoved two fingers right into her clit and rubbed furiously, huffing as she listened to the scene going on next door.</p><p>In Andy and Carol's apartment, Carol ha finished with the preliminary work, sort of. She had ordered Andy on his back while she tore off her hands, straddling the boy's face with her ass. Andy looked up and saw Carol's now familiar dirt star a mere few inches from his face.</p><p>"Now Bianca, good sissies service their mistresses in every way that they can, and that includes when they wish to sit on your face. So you are going to lick my asshole until I am satisfied, got it?"</p><p>"Yes Mistress" Andy nodded.</p><p>Carol dropped her ass and her perfect asshole hit and right in the mouth. He started to kiss and suck her hole before sticking out his tongue and rimming her sides. Carol's large cock was now in full view and she started to stroke it.</p><p>"Yes Bianca. Good girl, lick me just like that" Carol cooed.</p><p>Andy continued his good work, again kind of wishing it was Riley who was smothering him, but he enjoyed being able to grab Carol's massive cheeks while she shouted commands at him. After another moment, Carol lifted herself off of Andy to get a breath.</p><p>"Catch your breath, and lick my balls" she ordered.</p><p>Andy got a few deep breaths before Carol moved her ball sack into his open mouth while Andy tongued and played with them, making Carol giggle. She continued to furiously stroke herself while Andy tongued her sack.</p><p>Back at Riley's, she had to aggressively bite her lip to avoid moaning loudly while she was masturbating to the sexy times going on next door to her. She grunted, massaging her labia and herself wishing she was driving Andy's—sorry, Bianca's head into her pussy.</p><p>Riley's own need to dominate probably came from an overbearing upbringing caused by years of neglect and anger brought on by her parents, who she seemed to resent. Anything that made her upset she would manifest into pure rage, and it would often need to be released sexually. But out of all the times she could have released some sexual tension she had to try and punish the sissy begging for her to fuck him by not fucking him at all.</p><p>She thought of her relationship with men and what brought her up to this point in time and the results were not pretty. An overworked and mildly alcoholic father meshed with a chaotic home life and coupled with a string of bad relationships through high school made for one mean dominatrix in her twenties lazily coasting through life otherwise. God she wished she wasn't so stubborn and headstrong.</p><p>Over with Andy, he was now being smothered by Carol's tush yet again. Carol had taken off her shirt and bra, now being completely naked. She smushed her ass right onto Andy's face for a few more moments and got off of him.</p><p>"Good girl, Bianca. Now then, let's train your pussy while I show you exactly what I got for you."</p><p>Carol lubed up Andy's asshole and shoved two fingers into it to help stretch him out. She flipped him onto his back and rested his ass against the bed, and more importantly, the cock of the dildo machine.</p><p>She activated the device, spreading Andy's cheeks out as the machine broke into his asshole and Andy moaned, getting the cock shoved in and out on it's own. After some brief thrusts trying to get past his initial opening, it subsided, and the cock slid into his rectum.</p><p>Carol released from his cheeks, giving them a playful slap and went over to her bags, dumping out their contents onto the bed in front of Andy who marveled at this collection while simultaneously getting fucked by the robotic cock.</p><p>"Look at what we have here" Carol held up each thing one by one. "A riding crop, so I can spank you while you suck my dick. We got some fuzzy handcuffs to bind those adorable wrists of yours. Some leg irons, a ball gag to shut that unruly moaning little mouth of yours. Ropes, chains, a few butt plugs so we can have your hole nice and stretched out for easy access. And a few dildoes" she pointed to two cocks in particular, one was a thick but fairly moderately sized suction cup dildo you would attach to a wall, the other was a free standing dildo, in brown, that was thin but much longer.</p><p>"Whooooooa" Andy moaned.</p><p>"And in the kitchen, I bought you some more outfits, I want you at least in panties exclusively by the end of the week, and soon we'll phase out your male wardrobe and at least have you in drag when around the house" Carol explained. She handed Andy the thick dildo. "Suck on it" she ordered.</p><p>Andy grabbed the cock and opened his mouth, shoveling it inside. He stared at Carol while slamming his face onto the cock, occasionally licking the tip and letting the saliva fall on the plastic and silicon toy.</p><p>Carol stroked herself again watching Andy suck the fake cock while the dildo machine stretched his ass out, all while in girly clothes and makeup. She cooed and blushed, as did Andy while giving his mouth a self-imposed fuck.</p><p>Riley heard all the chicaneries going on at her place. She now had a pocket vibrator she was using to masturbate with while she had shoved one of her butt plugs up her ass. She was getting close, forcing herself to bite down on her wrist in order not to scream.</p><p>God she was so pissed. If only he hadn't stolen from her. Sure it would have been an awkward meet regardless but at least she could have gotten past all that and forced Andy to bend over and take her strap-on, currently collecting dust instead of being rammed inside Andy's rectum.</p><p>Riley blushed. She could feel her legs buckle and tighten around her crotch. She bit down hard a she finally came, convulsing and moaning through her hand while her body writhed and cum leaked out of her vagina and onto the bed. After the most disappointing yet fulfilling orgasm had finally subsided riley dropped the small vibrator and let go of her wrist, which now had a massive bite mark on it from the pressure of her teeth. A sweaty and unfulfilled riley laid on her bed, still listening in on next door.</p><p>Back over there, Carol was now right behind Andy, still sucking on the cock, Carol was jerking off right over his ass while the lubed up dildo was still sliding in and out of him. Carol bit her lower lip.</p><p>"Yes, soon my little sissy slut, soon I am going to wreck your butt pussy. You are going to take every inch of my cock" she moaned. Andy nodded. "And I am going to fill your little rectum up with my seed. I want you to beg for my sperm in your ass" she continued to jerk herself, super close at this point.</p><p>Carol gritted her teeth as she could feet her cock throb, pre cum leaking from it. After some few final moans Carol could feel her load shoot out of her tip, landing perfectly across Andy's butt like Dexter splatters the blood of his victims on a wall. A few more shots landed on his cheeks and the dildo, while the last few drops dripped right in the middle of his crack. Andy took the dildo out of his mouth as he got goosebumps form Carol's warm jizz coating his sensitive rear.</p><p>"Good, now go clean yourself up, you're a disgrace" she deadpanned, turning off the dildo machine and sliding the cock out of Andy's asshole.</p><p>Andy sighed and nodded. While it wasn't the experience he was hoping for, it was still hot all the same. He still hoped there was something there between him and Riley, but figured he should just let it play out for now, not wanting to bother her so quickly...little did he know had he ran over there right then, Riley would have dragged him inside and fucked him silly, just the way he wanted it...but Andy didn't know Riley's dilemma and instead wiped Carol's cum off his butt as ordered, staring at himself in the bathroom mirror seeing his mascara and makeup running, just like his melting heart.</p>
  </div></div>
<a name="section0003"><h2>3. The Love Triangle Begins</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Summary for the Chapter:</b><blockquote class="userstuff">
            <p>Andy continues his sissy training as Carol becomes much more sadistic than he first thought, but his problems double when Riley starts to take notice of him and the two begin their own relationship. What could possibly go wrong?</p>
          </blockquote></div><div class="userstuff module">
    
    <p>We see Andy and Riley each in their respective showers. Andy let the water cascade on him, now without the wig and makeup. He still wore the cock cage though. He stared at it, desperately wanting to cum as he could feel his dick throb in the pain of blue balls.</p><p>Riley played with her breasts while trying to wash herself. She got visions of shoving Bianca against the shower wall and ramming his ass with her strap-on dick while the two showered. With a free hand she shoved two fingers inside her vagina.</p><p>Andy was soon joined by a naked Carol who affixed the suction cup dildo to the wall of the shower, which would have been perfect asshole height for either of them as Carol wasn't much taller than Andy. Carol played with his rear end while he washed himself. He was liking this newfound life of his, but there was just a part of him that really hoped Riley would be in it.</p><p>Some days past and Andy was adjusting quickly to being a bottom sissy slut. He was now wearing panties underneath his underwear and had a few outfits to wear around the house when he wasn't working or running errands, which were about all he needed to leave his apartment for.</p><p>Carol also typically had him wearing a butt plug inside of him whenever he wasn't cleaning/relieving himself, or had some other phallic device inside instead. Carol was focusing on training Andy's mouth, waiting for the right moment for her dick to get acquainted with Andy's rectum; a waiting game that was becoming agonizing to Andy, but he loved every blue ball busting moment of it.</p><p>Carol had been enjoying the riding crop and a cat o' nine tails she recently bought to spank the boy while he sucked her off. Recently Andy, as Bianca would be dressed in drag, plugged up with handcuffs and leg irons on his wrists and ankles while sucking off Carol, which made him particularly blush as he liked being restrained.</p><p>Carol threw back her arms on the back of the couch while she groaned in pleasure, looking down seeing Andy's head bob up and down on her cock, moistening it up and leaving a growing trail of saliva down the shaft.</p><p>"Suck harder" Carol ordered. "Come on bitch, deep throat the fucking thing!"</p><p>Carol threw her paw to the back of Andy's head and forced his face onto her dick. He started to gag as she forced his throat on her member just like old times but Andy learned a few tricks to relax and loosen up his jaw.</p><p>"Mmmm, good slut" now more satisfied she stroked the fake wig he wore. She looked down smiling seeing a wide eyed Andy staring up at her. A few tears dripped down his cheeks ostensibly from the deep throating. "You're getting much better at chugging cock, Bianca. You're a real—fast learner" she moaned, getting close as Andy was demonstrating impressive skill.</p><p>He got a better footing with his knees and lifted his cuffed hands up, each hand gripping Carol's schlong as he continued to massage her member with his tongue, really savoring the taste. This was starting to become muscle memory to him.</p><p>His tranny mistress took notice of Andy's obedience while she rubbed his wig getting her big cock sucked. Her ego grew exponentially from this experience and wanted as much humiliation out of Andy as she could squeeze. The power was really what got her off instead of, well; actually getting off.</p><p>"Ooooooh, Bianca, I'm getting so close honey" Carol cooed.</p><p>Andy felt her grip on his wig tighten while he felt her cock throb a little in his mouth and hands. Some drops of pre-cum had found their way out of her dong and onto his tongue. He slammed his mouth on her cock, his cuffed hands now squeezing her balls.</p><p>His mouth was nearly touching Carol's crotch, her dick was deep into his throat. Andy felt it tightening, more tears coming down his eyes as he kept the dick down there. Carol let one a final grunt.</p><p>"I'm cumming! I'm cumning!"</p><p>Andy clenched his eyes shut as two huge blasts of jizz were shot deep into his esophagus. Carol started to pull her throbbing dick out as another shot went into his mouth. Andy opened, some cum falling off his tongue as Carol shot wave after wave of hot creamy cum on his face, his wig, in his eye and down to his chin. She let the last few drops fall onto his tongue.</p><p>"Oh baby. Look at that slutty face" she mused, wiping her cum and saliva soaked cock all over Andy's mug, destroying his makeup. Satisfied, Carol stood up from the couch, forcing Andy to remain on his knees. "Don't move a muscle" Carol disappeared into her room and appeared moments later with an old camcorder. Andy looked up.</p><p>"Bianca, tell us what you like?"</p><p>"I like sucking on big tranny cock" Andy said in the girliest voice possible.</p><p>"And why do you like sucking on big tranny cock?"</p><p>"Because I'm a little sissy cumdump."</p><p>"Good girl. You like having cum smeared all over your face?"</p><p>"Oh yes. It makes me look naughty."</p><p>"Good. Now go clean yourself up you little whore."</p><p>"Yes, mistress" Andy was about to get up, but Carol pushed him back down.</p><p>"Crawl, bitch" Carol ordered. "I didn't give you permission to walk."</p><p>"Yes Mistress. Sorry Mistress" Andy got on all fours and crawled to the bathroom while Carol filmed his ass the entire way.</p><p>A few more days past, and Andy hadn't cum since Carol caged him up in the first place and Andy was desperate to get some sweet relief. But, he had laundry to do that day. Knowing he had things to do, he was in some dude clothes but had on a pair of silk panties, his cock cage, obviously, and stretching him out was a glass butt plug inside his rear.</p><p>In the apartment complex, there was a communal laundry room on the first floor, which was as humid and about as out of date and as dusty as you're picturing it. The smell of hot clothes and dryer lint was rampant inside this concrete room with several flickering lights.</p><p>Andy had a stack of quarters and his hamper. He started to throw his clothes, and some of Carol's into the basin. As he was finishing up he turned to his right and saw someone else was fortuitously doing some much needed laundry, too.</p><p>It was Riley, hamper in hand, lazily tossing her clothes inside the basin, too. As she was about to toss a Tide Pod in there like a laundry grenade, she turned next to her to see Andy not-so-subtly staring at her.</p><p>"What the fuck do you want?" she eloquently asked.</p><p>"Oh, sorry. Um, I uh, I couldn't help but uh, notice you were, you know, doing some laundry" he said awkwardly.</p><p>"Yeah, that's traditionally what one does in the laundry room" Riley nodded, not even wasting time for a good witty sarcastic and sardonic remark.</p><p>Boy was Andy striking out. It was funny, without the wig and the fifty pounds of makeup he was hardly recognizable out of glance. His confidence to just walk up and seduce Riley had been drained when he was his boy-ish self.</p><p>He knew he could penetrate Riley's tough-chick persona, but on his own, he was just some doofy looking wimpy dork. He started to sweat like he was in high school all over again, except this time he wouldn't get a drink thrown in his face, he might get Riley's fist in there.</p><p>"Hey, weirdo! Is this going anywhere or may I resume my life now?" Riley asked.</p><p>"Oh, sorry. Um, I saw you're uh, using Tide Pods. Great choice. Just uh, don't eat them" Andy said making a reference that was already out of date.</p><p>Riley raised an eyebrow. "Yeah, thanks there, chief. This may come as a shock to you but I'm not some inbred dumbass, nor am I two years old; I have a very firm grasp on the nuances of the proper uses for laundry pods" Riley sarcastically explained. "Any other stupid remarks? No? Great. Nice first date, bud. Good work" Riley sarcastically patted him on the shoulder and walked out the door. After she was gone for a moment, Andy, thinking she might still be around but kind of hoping she wasn't, decided to blurt this phrase: "I want you to fuck me!" Andy called, but Riley was clearly gone. "Son of a bitch" he facepalmed.</p><p>Riley never did hear him, because as far as Riley was concerned, he didn't exist, and more importantly, when she took a few seconds to acknowledge him, they were always awkward and their meetings would end in antagonism.</p><p>But there was something about the skimpy outfit, and wig that really gave Andy the boost he needed, he of course realized what he had to do to win Riley over, but Riley was oblivious to that fact, still kind of salty that she missed an opportunity to dominate Bianca who she ironically just rebuffed in his true form.</p><p>She slammed her apartment door and trudged to her room. She had recently bought a suction cup dildo of her own, especially after hearing Carol yammer on about theirs through their paper thin walls.</p><p>She attached it to her sliding glass mirror closet doors and had the dildo lined up with her pussy, maybe a quarter of an inch above. She slid her shorts down, and grabbed a bottle of lube. She greased up the silicon shaft and added some to her pussy and ass before guiding the tip against her snatch, and slowly let it penetrate her.</p><p>"Oh fuck yeah!" she winced.</p><p>Riley slowly slid the cock in and out of her pussy which at first was a bit tough to glide the large cock through, even with the lube. Slowly though, her sugar walls expanded and moistened themselves up.</p><p>Every few back thrusts, Riley could feel the cock grow ever so slightly inside of her. It also was much easier to glide it through and the deeper it went into her, the more it made Riley blush. She moaned.</p><p>"Yes, oh yes. Oh fuck me!"</p><p>See, Riley didn't mind bottoming, it's not like she's never been penetrated, Riley simply had an ego and a reputation. She was always seen as this very tough chick who took no guff from nobody, nohow. She wasn't going to let herself become so vulnerable that she would spread her legs for some scrub's dick. No, if Riley was going to be fucked she wanted to be fucked. She wanted to be railed by the kind of guy who backhands her before bending her over something and slamming his douche dick into her.</p><p>Riley wanted to be fucked by someone who was stronger than her in every way, or they weren't enough and were beneath her, thus she wanted to dominate them. As Riley had these high standards, she realized the best possible fuck she could have would be if she fucked herself, which Riley was no stranger at doing and might answer a few questions you may have about her.</p><p>She was growing impatient as she rubbed her clit furiously to the rhythm of her fucking herself with the mounted cock. Riley was yearning for something more taboo, something naughty that she could rally sink her teeth into.</p><p>"Fuck this" she squirmed, sliding the cock out of her snatch.</p><p>She moved the tip towards her ass. Riley used some fingers to stretch her hole open, so she bent over some more to make this easy. As she did, she moved the dick towards the opening. It was still so tight, and Riley blushed trying to get that thing in there...maybe Andy could give her some lessons.</p><p>Speaking of Andy, while Riley was trying to force a cock inside her ass, Andy was finally about to have his cherry truly popped by Carol's dong. Andy was in a Japanese schoolgirl's outfit mixed with a sailor's outfit, which was white with blue trim and a blue super short-barely-covers-anything mini skirt. He had on matching high socks with heels, no underwear, he wouldn't have needed it anyway. He also had a curly brown wig on with teal and blue highlights.</p><p>As an added wrinkle, because Carol is a sadistic bitch, She had Andy's wrists and ankles bound to each of the bedposts while on all fours, forcing his ass up in the air. He smiled and blushed as a large blue butt plug was inside of him instead of the glass one, and his cock wishing it could break out from its cage.</p><p>She had out the riding crop, playing with it in both her hands, bending the stick in an effort to taunt Andy. She was completely naked, her cock nearly hard and read to go. She played with the front of the crop, dangling it in front of Andy's face which was also done up in tons of glittery makeup.</p><p>"You've been waiting for this, haven't you, Bianca?"</p><p>"Oh yes. I've wanted your cock for so long, Mistress."</p><p>"And I feel like we barely know each other" Carol cooed. She then made a swat, landing on Andy's left cheek, causing him to wince and left a pink mark where the crop had been. Carol made a few more to each cheek, each time, Andy would wince, make a face, or squirm from his precarious and humiliating position.</p><p>Carol showed no mercy on his behind, leaving pink welts on his otherwise pale ass cheeks. Her cock was near full length, as she stroked it with her free hand, getting off to spanking her bound sissy's ass.</p><p>Carol jumped on the bed, and slowly pulled out the butt plug, which had a large base which made Andy wince hard when Carol pulled it out, leaving his hole perfectly agape. She moved her cock into position, sliding it down Andy's crack to further taunt him. She moved the tip into position as she spread his cheeks as wide as they could go.</p><p>"Are you ready for a real dick, my little sissy slut?"</p><p>"Yes! Pound my slutty ass" Andy begged.</p><p>Andy had been waiting for this for so long. Really long in fact. He initially sought the anal attention of a hot woman's strap-on, never really thinking he'd ever get rammed by a hot trans woman, and here he was.</p><p>He had been looking forward to this ever since Carol surprised him by slapping her cock in his face not so long ago. Now, properly having his anal cherry popped was about to become a reality. Carol lined up with his hole, still gaping from the plug and made a slow insertion.</p><p>It was slow at first, and even with his enlarged sphincter, Carol's slicked-up member slid right out, but she forced it in, and after getting the tip past the hole, his rectum ate up her dick. Carol moaned happily feeling Andy's tight walls against her dong.</p><p>"Oooooooh baby, such a tight little butt" Carol mused.</p><p>"God that's so big" Andy groaned, now feeling such a weird sensation he couldn't even concentrate on his Bianca voice and it sounded like a garbled slurring of words.</p><p>"You'll get used to it, bitch" Carol said, patting his rear with her hand, slowly making deep thrusts into him.</p><p>Meanwhile, over to a now naked Riley, she had finally gotten an extra lubed up wall mounted cock inside her rosebud. We get a good look at Riley's hot toned ass with voluptuous cheeks, a perfect ass for fucking.</p><p>She had finally gotten every inch of the cock inside her own rectum as it made weird sloppy noises reaching to that point. Riley pushed herself on and off the dildo, playing with her tits as she did.</p><p>In actuality she was hoping—praying in fact that she could fuck herself on this dildo while her strap-on was plowing Bianca's asshole, which was ironically being stuffed with Carol's dick at the moment.</p><p>She was twisting her nipples while moving her hips onto the cock shoved inside her asshole. Riley gritted her teeth and then bit her lower lip, slowly getting wetter and hotter from her self-imposed fucking.</p><p>"You little bitch" she sneered. "I'm gonna fucking destroy you!"</p><p>Riley moaned, now using a hand to rub herself, taking deeper thrusts into the cock, dripping with lube onto her floor. She pushed her ass so deep that her tushy was now against the cold mirror of the door. Riley blushed as her nude cheeks made contact with the glass.</p><p>"Oh fuck me" she cooed.</p><p>She was close. Her fantasies of being penetrated while fucking Bianca were growing as her regrets of shoving him off that day had reached a breaking point. If she had a DeLorean she'd be speeding down Laurel Canyon at 88 miles per hour to go back in time and stop herself from not properly punishing the sissy panty thief.</p><p>But as Riley was stuffing her pooper on the cock she had a thought. True, she didn't like pussified dudes fucking her, mostly because they wouldn't have the speeds to get her off, but she was curious about Bianca. There was something so alluring about her strange confidence and how she clearly wasn't frightened even when Riley was at her meanest. It felt almost like Bianca's charm could have put Riley in a submissive mood in a sense.</p><p>That's what made that all the more painful, as Riley was ready to orgasm. Her whole philosophy was being turned on its head in a way and she didn't know how to manifest these newfound feelings, and to add to the ironic cum-stained predicament Riley had pushed aside Bianca's alter ego like he was nothing.</p><p>"Ah-ah-ahhh-ahhhhhhhhhhh fffffffffuck!" Riley moaned as she came, her asshole clenching around the dick as her cum dripped out of her vagina. Riley leaned against the closet door, sweaty and not nearly as fulfilled as she wanted to be. She slid the greased up cock out of her ass, leaving it gaping in its wake. Riley sighed and went to go get a shower, the feeling of missed opportunity meshed with conflicting emotions filling her mind.</p><p>Back to Andy and Carol, the ladder was deep inside of the former's ass. Carol had dispensed with going fully in and out of Andy's bum and instead remained deep inside of his rectum, taking brief thrusts, maybe an inch or two, but never really pulling out of him.</p><p>Andy could feel her dick massaging his prostate, he was so desperate to cum but he knew he couldn't jerk off. Regardless, he felt like he was still close, being edged out for so long didn't stop his balls from wanting to explode, despite the fact that his cock couldn't expand because it was caged up.</p><p>"Ohhhhhh I wanna cum" Andy begged</p><p>"You can, my little cumdump" Carol cooed, petting his wig. "I want you to cum from anal stimulation. Unless I say otherwise, that's how you will release. You're my sissy pet Bianca, and—ohhhhhh-oh, sissy pets cum from getting their pussies destroyed" Carol moaned.</p><p>Andy liked the sound of that, the blush streaking across his face. He liked this feeling, being so helpless to simply take his mistress's dick up his butt. He felt his rectum close-in on Carol's member and that was sending her over the edge.</p><p>"Fuck!"</p><p>"Are you gonna cum?" Andy asked.</p><p>"Oh yeah you little shit! I'm gonna cum!"</p><p>"Cum inside me!" Andy begged.</p><p>Carol stopped dead in her tracks. Andy was HER submissive, and while this was benign and forwarding Andy's drained masculinity, it still sounded like a command instead of the obvious which was him begging to be creamed.</p><p>Nevertheless, Carol had to continue to establish her dominion over the hapless sissy and punish him for such a transgression. She pulled out of his ass with an audible pop and Andy moaned as it was not graceful nor gentle. Carol lined her throbbing cock over his rear and shot her load once again over his cheeks. The lines of cum dripping down off of Andy's tush and onto the bed.</p><p>"Wha-what happened?" Andy asked, being denied an orgasm himself. "I-I-I-I thought you were gonna cu—"</p><p>He was interrupted by Carol moving to the other side of the bed and cupping him by the chin. She slapped him across the face. "You don't tell me where I can cum. You are mine, you understand, Bianca? I tell you what to do, not the other way around, got it!?"</p><p>Andy was a bit scared by this suddenly shift in Carol's mood. She had been domineering before, but this seemed extreme. Not wanting more punishment, Andy tried to stay in character as his eyes welled up with tears.</p><p>"G-got it. Sorry, M-M-M-Miss-tress."</p><p>"You'd better be. As punishment I am going to leave you in this position all night. I'll unhook you in the morning. Take this time to think about who you belong to" she warned, leaving Andy bound to the bed, still in his schoolgirl outfit, with Carol's jizz dripping down his ass.</p><p>Riley had gone to bed that night, rubbing herself to sleep, hoping to one day have another run-in with Bianca. She feared since putting the fear of God into her that Bianca wouldn't want to steal from her again, so her only real recourse would be to just knock on her front door and...and what?</p><p>What would she do? Riley was too proud and over-confident to ask for a pity fuck, especially from a sub, but how could she just make conversation that would lead to a meeting? Nobody goes over to their neighbor's house to borrow a cup of sugar anymore, and Riley couldn't think of any real reason to just knock.</p><p>She sighed, abandoning her masturbation and hoped her path would cross with this strange sissy again. For Andy, he remained bound to the bed, still in girly clothes, but Carol's cum had now dried and it just felt like something dry and sticky covering his ass. Carol had stopped by before bed briefly and wordlessly shoved the butt plug back inside of him to keep him nice and loose for future poundings.</p><p>He wasn't having second thoughts about being Carol's bitch...right? He was enjoying being dominated by the bubbly Carol but there was something about her demeanor that was getting more and more controlling.</p><p>The big red flag was Carol misconstruing Andy begging to be creamed by her cum as to mean he was giving her an order, the price of which he was now paying. But, he put those thoughts out of his head for now and tried to get some sleep in this most compromising position.</p><p>The days had past, and Andy was slowly wearing his girly clothes and makeup more and more around the house. It had been a few weeks since he began this journey and he was now wearing girls clothes completely around the house, having a few male shirts and shorts for when he had to leave, but he now had no more briefs, and exclusively wore panties regardless of if he was in the apartment or not.</p><p>He was also rarely with anything not up his ass, typically having a plug inside of him whenever possible. Andy was in a girly outfit doing some laundry which he had finished. He was wearing the dark wig, along with a midriff and yoga pants. Carol had gotten him a fake set of boobs which she affixed to his chest. Andy still hadn't cum in weeks, as this notion of cumming from anal stimulation was actually kind of new to him. Carol had punished him for not cumming from getting fucked by not properly cumming in his ass yet.</p><p>Anyway, Andy was about to go to his apartment. Riley was in her kitchen, finally tending to the Mount Everest of dirty dishes in her sink. There was a window right above it, leading to the hallway outside. She glanced up and happened to see Andy walk past.</p><p>Riley felt this weird sexual sensation cascading over her. She quickly washed her pruned hands and haphazardly fixed her hair, borderline relegating herself to that thirsty schoolgirl who wants the star quarterback's dick.</p><p>She ran out of her apartment, but composed herself to try and make the situation look organic. "Bianca, right?" Riley asked in an over-eager voice.</p><p>Andy stopped dead in his tracks as his front door was halfway open. Wow, Riley, his crush was standing outside and talking to him! Well...I mean, she was talking to Bianca, which was him by association. He felt weird, she had never done this before.</p><p>Andy was overjoyed to say the least, he wanted to throw cosh into the wind and make out with her, something Riley wouldn't object to, but then he paused. But then again, this was his alter sissy ego she was clearly thirsty for...not Andy. And yeah, there was a part of Bianca that was real, but it was mostly a persona he'd created, and ironically for the purpose of getting to know Riley. But there was something making Andy feel uneasy. There was the way Riley was so dismissive of who he was outside of this over-confident persona that it felt like it wasn't fair. Like there was only half of Andy Riley was attracted to.</p><p>Andy gulped. His dick wanted to just cream himself inside of his tight yoga pants, but a part of him wanted some revenge, and it would be perfect because it puts them on a level playing field and Andy could feel Riley out, he felt like rejecting her would shatter her own ego and make her that much thirstier for him. He smirked, impromptu plan set in motion.</p><p>"Yes, may I help you?" he asked in his girly Bianca voice.</p><p>"Oh um, I uh, saw you and..." she stammered. "I wanted to say I'm sorry, for the way I treated you last time."</p><p>Andy wished this apology was for her attitude in the laundry room, but he knew it was her woman-handling him in their first encounter. "That's fine, you were well within your rights. I did steal from you. Apology accepted. Anything else?" Andy asked. There was no answer as he could tell she was racking her brain trying to think of something to say. "No. Good" he parroted her response from before was about to walk into his apartment when Riley again stopped him.</p><p>"Wait!" she said. Andy smirked, but then put on a solemn face. "Look, maybe you and I got off on the wrong foot before."</p><p>"That's one way of putting it" Andy deadpanned.</p><p>"But like, I'm sorry, you know, maybe we can, like, get to know each other better. Maybe it doesn't have to be so awkward, you know? I mean, we are neighbors."</p><p>So much irony. Had this've been Andy, Riley wouldn't have even looked up from cleaning her dishes let alone throwing herself in his doorway to make time with him. But Andy knew this was how he was going to get some sweet, sweet karmic revenge.</p><p>"Well, you seemed pretty hellbent on putting some fear into me and it worked, I will not take your things without asking, again sorry; but it felt obvious that you don't want anything to do with me. Now if you'll excuse me, I have some ironing to do" Andy tried to get inside, and again, Riley stopped him.</p><p>"Don't be like that" Riley mumbled, almost sounding like she was begging.</p><p>"I do believe your words were "If I stole from you again, I could forget the cops, because you would just kill me", does that sound right to you?"</p><p>"Come on man, I was pissed—you took my panties! How was I supposed to react? "Hey, that's cute ha-ha, look at you wearing stolen property, wanna bang?" What did you want me to do?" Riley asked.</p><p>"Like I said, I was in the wrong, I admit that, but you didn't sound like you wanted anything to do with me, and I don't want to cause you more trouble" Andy insisted.</p><p>"It's no trouble. I'm over it."</p><p>"Look, you seem like a nice woman, but I'm just not interested right now" Andy stated.</p><p>That broke Riley's little heart. She really regretted that day now, not realizing this revenge tactic was a reprisal for not giving Andy the time of day in the laundry room. Her anger was growing, and she grabbed Andy by the wrist. He smirked.</p><p>"You're crowding me" he stated.</p><p>"Listen you little shit, I had a right to be angry, and I said some incendiary things, I admit it, but you think you can treat me this way? I stop you from stealing my property and you think you can just give me the cold shoulder? As I recall you had that little sissy ass of yours bending over my couch begging me to peg you. So what's this now? You didn't get what YOU wanted and now I get nothing?"</p><p>"And what makes you think you're entitled to have sex with me when you please?" Andy asked. "What, you're over it and I just need to forget your seemingly credible threat and spread my cheeks for your dildo? I feared for my life after that."</p><p>Riley rolled her eyes. "Oh, poor you! Do you really think I was gonna kill you? Yeah, the Hispanic chick kills her weird crossdressing white neighbor because items totaling fifty dollars were stolen by him? That'll sway the jury" she sarcastically stated.</p><p>"You frightened me, and I feel like maybe I was barking up the wrong tree. Message received" Andy again was about to walk in, but this time, Riley got in front of him, crossing her arms as she blocked his path into his apartment. She put on the most serious and scary face she could.</p><p>"Why don't you just shut up and come to my apartment? That's what you really want."</p><p>"No, what I really want is to iron these clothes for my Mistress."</p><p>"I wasn't asking. Get. Inside. Now" Riley ordered.</p><p>Had this been that day, Andy would have been ecstatic. But he stuck to his guns, his ego at its height. He knew Riley was blowing smoke up his butt. In this form he wasn't scared of her anymore. She had already admitted to not having it in her to actually kill him so it stood to reason she was probably not going to kidnap and sexually assault him.</p><p>"No. Now move" Andy said with a bit of authority in his voice.</p><p>"I'm not gonna. I know what you want."</p><p>"Right now, it isn't you" Andy insisted.</p><p>"You can't be serious? All of my shit you stole to clearly get my attention and here I am giving it to you and I'm the one getting blocked?" Riley asked.</p><p>"It's nothing personal, Riley" Andy lied.</p><p>"Bullshit. Now why don't we forget about all this and you know, go to my place and get to know each other" she said, caressing Andy's wig.</p><p>"Oh, well I can make us tea and scones" Andy said semi-facetiously.</p><p>"You know what I fucking mean" Riley hissed. "You want to be fucked? I wanna fuck you. Let's work together."</p><p>Andy's lip quivered, but he quickly gulped and pushed past Riley into his apartment, which was a huge mistake because Riley entered in after him, closing the door behind them and made it a purpose to loudly turn the deadbolt lock. Andy sighed, loudly and dramatically dropping the hamper to the floor.</p><p>"You're not invited. This is an unlawful trespass."</p><p>"Call the cops, then" Riley egged him on, trying to establish control once more. She turned to the nearby kitchen table where conveniently Andy's phone sat. They eyed up the black silicon and glass brick. Riley lunged first, and grabbed it a split second before Andy could get to it.</p><p>"Dammit!" Andy groaned, desperately trying to stay in character.</p><p>"Of course, your phone is all the way over here" she cooed</p><p>"Give it to me!"</p><p>"Sure. But you gotta come and get it" Riley dropped the phone into her pants, now resting between her panties and crotch. Andy rolled his eyes. "You'd like the cops to come and put me in handcuffs, wouldn't you?"</p><p>Oh boy would he, but Andy didn't want to give her the satisfaction. He was in too deep now and a victory was about all he wanted. He was about to charge after Riley in a fit of repressed masculinity but before he could the two heard the sound of rummaging outside the door, and after a few moments the deadbolt unlocked and Carol strolled in.</p><p>"Bianca, I'm ho...who is this?"</p><p>"Oh um, this is our neighbor, Riley" Andy said his girl voice choking up.</p><p>"Hi, I'm Riley" she waved.</p><p>"And what is "Riley" doing here, exactly?"</p><p>The two stared blankly at one another. Riley had heard Carol's voice before as well as the sexual romps she had with Andy, most of the apartment complex did, but Riley could tell Carol was not in a welcoming mood...and for that matter didn't seem like such a welcoming person. So she decided it would be in her best interest to think of a plausible excuse.</p><p>"I had some shit stolen from my apartment, and I was just going around seeing if anybody knew anything, saw anything suspicious" she said matter-of-factly.</p><p>"I see. What a shame you were broken into? Was your door unlocked?" Carol asked, looking over at Andy who she knew was the culprit.</p><p>"Yeah, I'm kind of a fucking idiot, but I won't make that mistake anymore."</p><p>"I should hope not. Well I have not seen anything strange going around—Bianca?" Carol asked.</p><p>"Oh no, um, nothing out of the ordinary here" he chuckled nervously.</p><p>"Well, there you have it. Is there anything else we can help you with?" Carol condescendingly asked.</p><p>"No. That's all."</p><p>"Then you should be on your way, then" Carol insisted, opening up the door.</p><p>Riley took the hint. She looked over at Andy and glared at Carol as she walked out, door slamming behind her. But Riley immediately put her head to the door and could hear the carnage.</p><p>"What was that slut doing here!?" she heard Carol call.</p><p>"L-L-Like she said—"</p><p>"I know what she said you little tramp! I knew this would come back to bite you in the ass! What if she called the cops!?"</p><p>"She doesn't know!" Andy lied.</p><p>"She'd better fucking not! I told you to be careful, Bianca! That's bad! That's a bad girl, letting that whore in our house!"</p><p>"Ow-ow-ow-ow!" Riley could hear Andy being dragged by the wig as he was taken to his own room. Riley gulped, and slowly backed into her own apartment. When she got back she realized she still had Andy's phone inside her pants.</p><p>"Aw shit" she groaned. She could hear the beating unfold from inside her apartment, it was the familiar sound of a cat o nine tails whipping somebody's ass. Riley sighed, this was not the best time to walk back over there. "At least I have a reason to go back now" she shrugged.</p><p>She tossed the phone aside and once again flopped on her bed, ignoring the dirty dishes she had previously spent weeks ignoring already. While she laid comfortably but unfulfilled on her bed, Andy felt very fulfilled...as he was getting whipped by Carol's cat o nine tails while he was bound with a ball gag stuffed into his mouth and the stationary dildo shoved up his ass.</p><p>"Don't lie to me!" Carol fumed. "That bitch came over to make time with you, didn't she!?"</p><p>Andy obviously couldn't answer, not that it made any one bit of difference though, Carol was just upset, and he was forced to take a beating. Eventually Carol stopped when Andy's tush was bruised red.</p><p>Carol undid his restraints, but left the dildo inside of him, she laid next to her sissy fucktoy, stroking his hair while tears of pain fell down his face, running his makeup. "I just don't want you to lie to me, Bianca. Now tell me the truth, why was she in OUR apartment?"</p><p>"I'm telling you the truth" Andy said, choking up from crying.</p><p>To be fair, Carol didn't have a reason not to believe him, but she wasn't convinced. She knew this was the neighbor Andy pined for and whom Carol was ostensibly training him to please...but that quickly grew into wanting Andy all to herself, and hoped he would abandon the idea of Riley in his life and only be with her. And Carol figured the only way to accomplish this was to make Andy not want Riley anymore, by punishing him if he did.</p><p>"The whole truth?" Carol asked.</p><p>"Okay, she came over wanting to ask about the thief that she didn't know about. And she commented on my outfit, but nothing happened" he explained, still kind of lying.</p><p>"I'll bet something would have happened had I not showed up, hmm?" Carol coyly asked.</p><p>"No, I swear, I was actually trying to get her to leave!" Andy admitted, which was completely accurate but not simply just to shoe her away.</p><p>Since this was the truth technically, Carol could feel it in Andy's voice. She nodded. "I believe you" she then grabbed him by the face. "But so help me, she is never here without my permission—not her, or anyone else? Understand, Bianca?" she asked, forcing Andy to nod. "Good girl. Now help me with dinner."</p><p>"Yes, Mistress" Andy mumbled.</p><p>Carol got up and walked out leaving Andy once again sexually pleased and in pain. A split screen shows us him and Riley laying in their respective beds, both wishing that afternoon went a little bit differently than it had.</p><p>But the next day came. Carol was once again out, but this time working, and Andy was going to grab a thing or two from the grocery store, and as such, barring the cock cage, butt plug and panties, was in male clothes.</p><p>As he was about to leave he opened the door, completely forgetting about his cellphone from the previous day, which is to say Carol punished him so hard he actually forgot that Riley still had his phone. Literally, as he opened the door, Riley was right there about to knock, the two were in a standoff once more.</p><p>Only this time, it wasn't Bianca Riley was looking at, it was Andy, and she was a tad bewildered to see him leave the apartment as she was clearly expecting someone else. "Oh, hey" he muttered.</p><p>"You? Weird laundry room guy?"</p><p>"That's me" a depressed Andy deadpanned.</p><p>"Wait...does..." Riley paused, looked at Andy's eyes. She then did the math in her head, and made a heavy sigh. "Oh my God. Oh my effing God!" she rubbed her temples.</p><p>Riley couldn't believe it, here was the most awkward, most dorky guy in the world, who with a quick wardrobe change turned him into the sassiest most confident crossdresser she had ever seen, and she's seen all episodes of RuPaul's Drag Race.</p><p>"So, this is the real Bianca?"</p><p>"Guilty."</p><p>"Wow. That's what yesterday was really about, huh? I ignored you and apparently have been ignoring you and you decided to get a little revenge. Am I in the ballpark?"</p><p>"Again, guilty."</p><p>There was an awkward pause for a few moments which seemed like forever. Riley snapped out of it and held up Andy's phone. "Oh hey, your um, your phone. Sorry, I was kind of rushed out of there and I forgot I shoved this into my pants" Riley explained realizing the situation was much more gross the second day than sexual.</p><p>"It's okay" Andy chuckled, taking the phone back.</p><p>"I um, I took a few wipes to it, it kind of smelled like vagina. I was really-really wet" she admitted, slight blush appearing.</p><p>"I noticed, trust me."</p><p>More awkward silence ensued, but Andy wasn't going to let the opportunity slip by him again. Sure, it was Carol who put the fear of God into him this go-around but he knew her work schedule, she wasn't going to be back anytime soon. And he was a little salty and scared of her at the moment, so a bit of rebellion while ill-advised was just the kind of boost his ego needed.</p><p>"You want to come in?" he asked.</p><p>"Yeah, thanks"</p><p>Andy ushered Riley inside, but he looked around to see if anybody saw her come in, spoiler alert, nobody did or cared. He closed the door behind him. "Would you like a drink? I can make you a drink-drink, we have some tequila" Andy awkwardly offered.</p><p>"Um, I was thinking something a little more potent and definitely more therapeutic" Riley smirked, taking a vape pen from her pocket. It was clearly a weed vape.</p><p>A few toks later, and the two were feeling comfortably numb. They sat on Andy's couch, ironically listening to some Pink Floyd on the television connected to Andy's phone. Riley finally spoke.</p><p>"I wondered at first how you knew about me" she turned her head. "But our fucking walls, man."</p><p>"Yo, it's like they're not even there! I can hear everything!" a high Andy agreed.</p><p>Riley took another hit. "Be honest with me, Andy" Riley said, finally referring to him by his name. "How long have you been stealing my shit? I'm not gonna get mad, I'm over that, but I gotsta know."</p><p>"Few months."</p><p>"How much did you take?"</p><p>"A lot. Those panties, the stockings, and the corset were the stuff I kept for longer than just taking pictures of myself masturbating in them."</p><p>"God, that's so pathetic" Riley blurted, not realizing it cut a little deep. "Sorry."</p><p>"Nah, forget about it. It was pathetic" Andy sighed. "I'm pathetic."</p><p>"Stop! No you're not!"</p><p>"I'm a Lyft driver with no goals or ambitions other than dressing like a women hoping some dominatrix ass fucks me with a strap-on and pours hot wax on my chest!"</p><p>"Hey, take it from me, the whole waxing craze is overrated."</p><p>"Regardless, you're right, I'm pretty pathetic."</p><p>"You want pathetic? This apartment is immaculate, you've seen my place I'm the laziest pile of shit in the world. I work at Buffalo Wild Wings, no goals, no nothing."</p><p>"Then I guess were one in the same?" Andy shrugged.</p><p>"Hurray, I guess we are both pathetic" Riley chuckled. "Can I ask a personal question?"</p><p>"Sure. Anything."</p><p>"Why do you like that? Being feminized and fucked like a girl? What does that do for you? I mean, you know me, I do that to dudes all the time but they never tell me why, usually about how much of a loser their wives think they are or some stock tip they came across. I think they're just too embarrassed, just wanna get humped, wham, bam, thank you ma'am, get their street clothes on and leave. I've never actually had the chance to ask."</p><p>Andy thought for a moment. "I dunno, it's kind of hot, being the girl. I can't really explain it, I just really get off to a hot chick in rubber boots fucking a dudes cornhole with a strap-on."</p><p>Riley chuckled. "Cornhole. How fucking old are you?"</p><p>"Twenty."</p><p>"It shows" she laughed some more, than playfully punched his arm. "I'm messing with you."</p><p>"I know."</p><p>"Don't take this the wrong way, Andy; and I mean this with...I mean this with all due respect: what is up with your psycho Mistress/roommate?" Riley asked, taking another drag. "Your relationship literally sounds like something out of a bad BDSM porno. What do you see in her?"</p><p>Andy raised an eyebrow, like it wasn't already obvious. "She's a fucking bombshell."</p><p>"Yeah okay, but what else? Trust me on this, I'm not much older than you, but I'm a little fucked up and I've been around the block a time or two; hotness is great in the honeymoon phase, but once that's over it won't make much difference, if there's a character flaw it'll only get worse unless there's something else there worth loving."</p><p>Andy shrugged. "I dunno. It started out nice, I guess. To be honest, she was supposed to be training me to be a submissive so I could have the courage to talk to you. But I guess it didn't take much."</p><p>Riley smiled. "You're real sweet...but kind of salty, like a pretzel dipped in chocolate."</p><p>"Those sound fucking dope right about now" Andy slurred, munchies taking over.</p><p>"Oh I know, right"</p><p>Riley spread herself out on the couch, which Andy immediately took notice to. "You want this, right?"</p><p>"Do you want this?" Andy asked, pointing all along his bod.</p><p>"Oh yeah. Why don't you show me what you learned in this sissy training. Come on" Riley asked.</p><p>"I dunno—"</p><p>"Andyyyyyyyy" Riley groaned. "You said so yourself she was training you for me. By association, I have the right to monitor your progress, and as such I demand to know how well you can take some fingers in your ass" Riley wriggled her digits.</p><p>In his inebriated state, that absolutely made perfect sense to Andy. Unfortunately he knew deep down this wouldn't go unpunished by Carol if she found out, and that alone was turning Andy away.</p><p>"I dunno, if Carol finds out—"</p><p>"She won't. She's working, right? We can be done in a few hours. Does she come home for lunch?" Riley asked.</p><p>"No, never."</p><p>"Then what's the harm?"</p><p>"She'll shove half her arm inside of me, then do the same to you...and then murder us, maybe—she's giving me really mixed signals lately" a suddenly paranoid Andy complained.</p><p>He threw his head on the back of the couch. Riley crawled up to him and looked at him square in the face. "If you're already nervous, maybe Carol isn't right for you."</p><p>"I've committed myself to her, though."</p><p>"This may be a fetish but you don't have a blood pact. You can just leave."</p><p>"She's my roommate."</p><p>"Who's name is on the lease?"</p><p>Andy sighed. "Mine."</p><p>"You're an adult, just kick her out."</p><p>"Wait-wait! You're acting as though I like, hate her, or some shit."</p><p>"You just said she's giving you mixed signals. I can tell she's controlling. You need to get out while the getting is good" Riley urged him.</p><p>She was admittedly doing this for selfish reasons. If Riley sways Andy away from Carol who clearly won't share him, then then she can have Andy and Bianca all to herself. But she knew this had to be the best move, right or wrong.</p><p>"I don't hate her. Maybe I can find something. She's still hot, and she is nice to me. It's just sometimes during sex she can be very aggressive" Andy explained.</p><p>Riley rolled her eyes, she leaned up and plowed her lips into Andy's in order to shut him up. Andy moved his hands around Riley's back and swirled his tongue inside her mouth. Riley responded by re-establishing her dominance, shoving Andy's tongue deep into the back of his mouth. She released.</p><p>"Wow, was that Andy, or Bianca?" she asked.</p><p>"Maybe it's both" he made a smirk after his cliched line.</p><p>"Bring her out more often, that'll boost your confidence, I know it. And maybe you can stick it to Carol with that newfound ego, huh?"</p><p>"I mean, I guess you're right."</p><p>"Of course I am. Now then, that kiss was down payment for today's lesson" she said, sliding off her shorts and panties, spreading her legs out wide. She gently rubbed her perfect clit.</p><p>"L-L-L-Lessons?" Andy asked.</p><p>"Carol's training you for me. We both know she won't find out, so why don't we stop tricking ourselves and do what we both know we want. Look, I'm sorry about being a dick to you. But to be honest, it's been nice getting to know you. I feel like we can do more of that. You, me, and Bianca."</p><p>Andy blushed. He didn't have a better excuse or anything better to do. Besides, this was what he wanted anyway, truly. Andy got on his stomach and slowly ducked his head towards Riley's moist pussy.</p><p>She of course had little patience and shoved Andy's head right in there. Andy shot out his tongue, wrapping it around Riley's inner folds. "Alright, now find the clit...find my G-spot" Riley cooed.</p><p>Andy kissed and slobbered all over her vagina, he eventually found what he sought after, Riley's extremely sensitive area. "Yeah, that's good. Yeah, use that—ooh, use that Bianca-power-bottom energy" she winked.</p><p>Andy did too and went back to licking his first vagina, which was a taste he could get used to. He savored Riley's pussy juices, so much so he got greedy and shoved a couple fingers inside her vagina, it's impressive he knew where the hole was.</p><p>Unlike Carol, Riley was perfectly content with this random care she was getting that she didn't ask for. She rubbed herself faster and harder to the tune of Andy giving her the best amateur head of her life. Even though he was inexperienced, Andy was a quick study.</p><p>"Oh yes. Oh-ohhhhhhh yes! Oh fuck!"</p><p>Andy didn't stop there, he shoved his digits in deeper, twirling his fingers all up in Riley's sugar walls. She moaned violently, but she didn't want to cum just yet, she forced Andy's head off her before it was too late.</p><p>"What's wrong? Did I do something?" he asked, frantically trying to catch a breath.</p><p>"No, no. You were great" she huffed, leaning up to give him a kiss., and rubbing his hair. "Stand against the wall" she smirked, "Stick that ass out."</p><p>"Yes ma'am" Andy nodded and did as directed, putting his hands against the wall and sticking his tush out. He could feel the plug clench inside of his ass. Riley got up and pulled down Andy's shorts and panties, groping and admiring his ass.</p><p>"What a fucking butt! That's a bottom butt right there" she said slapping his cheeks. "So girly and feminine I can hardly tell you're a guy" she chuckled, stretching them apart, revealing the butt plug. "What a slut. Always ready to get pounded, huh?" she asked, biting his melons.</p><p>"My pussy always needs to be ready" Andy joked, dipping into the Bianca voice for a moment.</p><p>"Has Carol ever, you know, put a cum baby inside you?"</p><p>"Nope, not yet, surprisingly."</p><p>Riley spun him around, revealing the cock cage. "Wow, still on, huh?"</p><p>"Never been off. I haven't came in weeks" Andy complained.</p><p>"Even from anal?"</p><p>"Tried that."</p><p>"Then you're doing it wrong, come on" Riley took him by the hand and she led him towards the bedrooms, where she remembered which one was Andy's from before. "Okay, if you're going to fuck yourself on a dildo, you should look the part."</p><p>They rummaged through Andy's closet and pulled out an outfit, along with his fake tits. It was a short and sheer night gown that stopped right at the ass, and a pair of long rainbow socks. Riley expertly applied Andy's makeup and lipstick before throwing the black wig securely over his head.</p><p>Now completely naked Riley led him over to the bed while Andy got out two of their stationary dildos, placing them on the bed. She jumped, trying to steady herself over the dildo, she lubed up a finger and shoved two in to stretch herself out slightly while guiding the dick to her sphincter. It was slow goings but the first inch got its way inside and gravity did the rest.</p><p>"It's nooooooot so bad" Riley moaned, bouncing. "You even have a plug, too. Come on, you gotta get the angle right, you'll cum every time."</p><p>Andy hopped up on the bed, sliding the plug out of his greased ass. He added some to the dick and his hole was gaping enough for the cock to glide right on in there. Andy blushed, slowly getting one inch or two at a time inside until he was able to sit on the whole thing.</p><p>"There you go, Bianca. You're handling it."</p><p>Andy grabbed her by the wrist, a little force in his voice. "It's Andy" he winked.</p><p>The two blushed and pounded their asses on the dildos. Riley started to rub herself while Andy fucked himself harder, hoping for some prostate stimulation. He was getting close, he could feel his balls ready to burst like a damn. It hurt so much.</p><p>"I'm so...I think I'm...wow! That's a good position!" he angled himself up just enough and gritted his teeth. "Fuck, I'm gonna cum!"</p><p>"Ahhhhhhh! Dammit, me too!"</p><p>Riley burst, squirting her feminine load all over the bed sheets, splattering like water color paints on a fresh portrait. Andy felt like his bursts were small and controlled, but after a squirt or two he could see the leaking juices falling out of the tip opening of the cage, it leaked all over the bed. Riley crawled over and licked it up as it fell, Andy smiled and fell over, the two no longer being impaled by the dildos. Riley jumped up and laid next to him.</p><p>"So, Andy...still apprehensive about training?" she asked.</p><p>Andy smiled.</p><p>So Andy agreed for Riley to also train him in secret. The two had also grown closer to one another this time whereas Andy felt he was just a piece of ass to Carol who didn't seem to want to do more than fuck him. And she still never came in his ass.</p><p>Andy knew his relationship status with Carol didn't seem more than roommate fuck buddies, which is what he kept on telling himself. Meanwhile with Riley, what he thought would be a dom/sub relationship was actually kind of a cute relationship. The two had a lot in common and were in fact very kinky. As the days rolled on, Riley slowly but surely started to dominate Andy the way he wanted, and Riley didn't mind being a sort of a bottom herself.</p><p>Andy would love giving some attention to Riley's pussy where she laid in a variety of positions while he licked her. But their mutual favorite was Riley facesitting on Andy's mug while the boy would be forced to lick her pussy and ass.</p><p>Andy even got to rest his rear end on Riley's face and she got smothered by his gaping asshole for a change, which Andy relished in, making it easier to cum despite still being caged. Sometimes he would let his cum drip on Riley's chest while she tongued his hole and Andy would lick it off her boobs.</p><p>The two would dress Andy up in a variety of feminine clothes Carol had bought for Andy, and the two would have impromptu fashion shows while Riley dolled Andy up. Every time there would be an outfit change, Andy would bend his ass over and spread his cheeks while Riley would either finger, or dildo his ass.</p><p>Andy would sometimes ram his ass on the shower dildo while Riley made out with him, and he wasn't allowed to stop until he came, which actually didn't take so long as time went on, I wonder what changed?</p><p>Riley also acquainted Andy with her heart shaped paddle she uses for spankings. She would bend Andy over something and properly wallop his bottom while he was bound and had a ball gag in his mouth. But the joke would be on Riley as Andy would turn the tables and do the same to her.</p><p>The best was when the two were ass to ass on a double sided dildo, stretching their asses out and the two of them thrusting back, bumping their butts into one another, both blushing. But this was their favorite thing.</p><p>"First one to cum loses, and winner spanks the loser" Riley said.</p><p>"I like those odds" Andy winked.</p><p>Andy of course lost.</p><p>The time continued, and Andy was ready to be pegged properly by Riley. Andy waited for Carol to go out drinking one night with her friends.</p><p>"Awwww, you're going out?" Andy asked.</p><p>"Just a for a few drinks. I'll be back, okay."</p><p>"When?" Andy asked.</p><p>"I dunno, midnight? Why?"</p><p>"I'd like to be ready for you, maybe have some drunk sex?"</p><p>Carol cooed, finishing fixing her hair. "I like where your head's at my little sissy pet. I'll be back" she patted his face and slowly heading for the door. Andy could see some apprehension in Carol's voice, but didn't think anything of it. He sneaked into her room and on top of her dresser, lazily sitting out was something that made him smirk. After she left, Riley sneaked over. The door opened up.</p><p>"Hey you."</p><p>"Hey yourself."</p><p>Riley was in the ultimate leather dominatrix outfit. She had on long black gloves and knee high boots with the formerly stolen fishnet stockings, the black corset with some black makeup, and a purple strap-on cock on a harness around her waist.</p><p>Andy had on a frilly midriff and black booty shorts with really high tube socks, and a curly blonde wig. He was definitely in his Bianca persona. Obviously he had on his cage and a butt plug.</p><p>He ushered Riley inside and slammed the door, he held up a set of keys. "I found these on Carol's dresser. It's to the cage" he winked.</p><p>"Ooh, that's naughty, why don't we test that out" Riley grabbed him by the hand and pulled Andy into his room, forcing him to bend over the bed. She immediately pulled his booty shorts and panties down and laid some hard smacks on his behind with the paddle.</p><p>"Ah yes! I'm such a bad girl" he moaned, Bianca checking in.</p><p>"Yeah you are!" Riley hissed, slapping his rear again and again. Finally she tossed it aside, and spun Andy around. He handed Riley the keys and she bent over to shove the key into the lock, she undid it and the cage fell right off, Andy's dick dripping wet and was immediately nearly hard from finally being freed.</p><p>"Awwwwww, that feels amazing" he moaned.</p><p>"Then this is going to feel even better" Riley said.</p><p>She bent down on her knees and gulped up Andy's dick in her mouth. It was sweaty and underwhelming as you would expect, but Riley could handle it, and the sissified Andy loved getting his dick sucked.</p><p>Carol never sucked him off. Andy cooed and gripped the sheets as Riley's lips over his dick felt so good as she deepthroated him. But this wasn't any ordinary blowjob. Riley slapped his balls and made a few tiny nibbles up his shaft, which despite the slight pain Andy moaned even harder.</p><p>Riley was also using a free hand to play with his butt plug. She got off of him and removed the plug quickly, lining up her freshly lubed dick with his hole. "Are you ready, Andy?"</p><p>"I'm so ready, babe"</p><p>Good"</p><p>"Ohhhhhhhhh!"</p><p>Riley plunged her dick into Andy's ass while he laid on his back. Riley jumped on top of him and thrusted her dildo deeper and deeper inside of Andy, which given the position he was in was quite manageable.</p><p>"Oh wow."</p><p>"Nice, right?"</p><p>Riley slammed harder into him, reaching down and making out with him while moving her hips. She could feel little drips of pre-cum leaking out of Andy's dick and onto her corset from the constant fucking.</p><p>"Yes! Fuck me!"</p><p>Riley slowly pulled out of Andy, and wanted a different position. Riley sat on the edge of the bed and Andy got the idea. He straddled her cock, his ass facing away from her and Riley lined the cock up and Andy sat right down on it.</p><p>"Oh fuck yeah!"</p><p>"Now bounce your ass!" Riley huffed.</p><p>Andy nodded and held his cheeks out with his hands while moving his hips up and down, bouncing them on Riley's strap-on. He grunted and looked down at his hot dominatrix girlfriend slammed himself harder and harder on the bed as he could.</p><p>"Yes! Fuck my ass!"</p><p>"Bounce harder you beautiful slut!" Riley hissed.</p><p>Andy continued, his dick aimed right at Riley. Andy smirked, he leaned on a different angle, the one that made him cum on command before and slammed his ass down, immediately stimulating his prostate, and his dick throbbed. Andy grunted, drool escaping his mouth.</p><p>"AHHHHHHH fuck!"</p><p>His sperm shot out of his dick like a shotgun, hitting Riley directly on her chest and face, all his drops falling down onto her. As he finally finished up, Andy was going to lean in for a kiss when the two stopped. They heard the familiar sound of rummaging outside the front door.</p><p>"Who is that?" Riley scream-whispered.</p><p>"I don't know?"</p><p>"Is it Carol?"</p><p>"Again, I don't know!"</p><p>"We gotta hide!"</p><p>"You gotta hide!" Andy insisted. He got himself off of Riley, and cum still on her, he pushed Riley into his sliding door closet, and quickly pushed the cock cage off the bed as he had no time to put it back on, his back faced the door as he heard footsteps coming in, it was Carol.</p><p>"Bianca" she said.</p><p>"Mistress, you're back early" Andy stated, nervously having his back to her in hopes she wouldn't see his dick not in the cage. "Really early."</p><p>"I turned around halfway there. I can't wait anymore!" she huffed.</p><p>She pushed Andy down to the edge of the bed with his ass sticking out. Riley cracked the door open and saw Carol disrobe herself, stroking her cock to full length. Carol spit on her dick and put the tip against Andy's anus, still puckering from being railed by Riley's strap-on.</p><p>"I see you were training" Carol cooed, oblivious to what he was actually up to. "Oh baby, I just had to, I had to make your ass mine" she whispered in his ear, groping one of his cheeks. "I'm gonna fill you with my cum"</p><p>Andy blushed as Carol forced the cock inside of his awaiting ass with no apparent warning, and Carol wasted no time picking herself up to full speed immediately, slamming herself into Andy's already spent rear.</p><p>"I'm so sorry baby!" Carol moaned. "I just wanted to...I just wanted to make sure you weren't—ahhhhh, with that little tramp, that's why I've been so distant!"</p><p>Andy couldn't even respond. All he could do was grip onto the bed sheets and bit down on them as Carol was relentless and not letting up. He could feel her dick expanding inside of him, tearing apart his rectum.</p><p>"Yes! Yeah baby, oh fuck yes!" Carol moaned. "We're gonna tattoo this ass tomorrow!" Carol mused, slapping his cheeks. "I can't wait to brand you mine!"</p><p>She could feel herself getting close, that's how long she waited for this moment, and her dick wasn't even locked in a cock cage. From in the closet, Riley still kept an eye out while sticking some fingers in between the harness to finger herself watching Andy get bent over doggy style by his shemale mistress.</p><p>"Oh baby, I'm gonna cum! Oh baby I'm gonna—cuuuuum! FUCK!"</p><p>"Oh cream in my sissy ass!" Andy begged, forgetting a slipup like that earned him a beatdown the last time.</p><p>But Carol was in orgasm mode and wasn't paying attention as she unloaded a torrent of baby gravy inside of Andy's butt, filling himself up with her seed. Andy felt like he was going to cum again from this strange new sensation filling his rectum up.</p><p>"Ohhhhhhhhh fuuuuuuuuuck" he moaned.</p><p>Carol was slowly finishing up. She pulled herself out of Andy's hole, which puckered once it did, and a droplet or two of cum escaped. As his ass contracted and his hole gaped, more and more of Carol's jizz leaked out of his bum, flowing down onto his balls. Carol ran to get her camcorder, and documented Andy's red ass dripping in her juices.</p><p>"You are mine, slut. How does that feel?"</p><p>"Oh, I love getting my pussy filled with your cum!" Andy called in the Bianca voice.</p><p>"Good girl" Carol said. She stopped filming, and turned her head, first noticing the cock cage Andy lazily threw onto the floor. Carol looked down. "Wait, what's that?"</p><p>Riley was still in the closet ready to cum again. Unfortunately, she lost her footing, not thinking of any of the consequences that could happen. As she lost her balance, she comically fell out of the closet, and Carol took immediate notice.</p><p>There were a few beats of uncomfortable silence. Riley said nothing. Andy's cum was still all over her but was starting to dry in places. Carol's blood boiled as she breathed deeply, her eyes locked onto Riley. She turned to Andy.</p><p>"What...the fuck...is SHE doing here!?" Carol scolded him. Andy gulped and blushed as Carol's cum continued to drip out of his butthole.</p>
  </div><div class="fff_chapter_notes fff_foot_notes"><b>Notes for the Chapter:</b><blockquote class="userstuff">
          <p>Last chance to get those tattoo suggestions in everyone! Thanks again for reading and for your patience!</p>
        </blockquote><b>Author's Note:</b><blockquote class="userstuff"><p>Leave a comment with your suggestions and they may be added in future chapters. Also, any suggestions for what Andy's ass tattoo should say?</p></blockquote></div></div>
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